[ CAS No. 106-65-0 ] {[proInfo.proName]}

Name: 106-65-0|Dimethyl succinate|99%
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Quality Control of [ 106-65-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 106-65-0 ]

Product Details of [ 106-65-0 ]

CAS No. :	106-65-0	MDL No. :	MFCD00008466
Formula :	C₆H₁₀O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MUXOBHXGJLMRAB-UHFFFAOYSA-N
M.W :	146.14	Pubchem ID :	7820
Synonyms :

Calculated chemistry of [ 106-65-0 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	33.53
TPSA :	52.6 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.94 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.96
Log Po/w (XLOGP3) :	0.35
Log Po/w (WLOGP) :	0.11
Log Po/w (MLOGP) :	0.25
Log Po/w (SILICOS-IT) :	0.38
Consensus Log Po/w :	0.61

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.64
Solubility :	33.7 mg/ml ; 0.231 mol/l
Class :	Very soluble
Log S (Ali) :	-1.02
Solubility :	14.0 mg/ml ; 0.0957 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.82
Solubility :	22.1 mg/ml ; 0.151 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 106-65-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P273-P280-P305+P351+P338-P337+P313-P501	UN#:	N/A
Hazard Statements:	H319-H413	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 106-65-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 106-65-0 ]
Downstream synthetic route of [ 106-65-0 ]

[ 106-65-0 ] Synthesis Path-Upstream 1~16

1
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[ 106-65-0 ]
[ 74729-01-4 ]
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[ 74729-02-5 ]

Reference： [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1981, vol. 30, # 6, p. 1054 - 1059[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1981, # 6, p. 1323 - 1328

2
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Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1980, p. 1636 - 1641
[2] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1980, p. 1636 - 1641

3
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[ 6149-45-7 ]
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[ 106-65-0 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1980, p. 1636 - 1641

4
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Reference： [1] Chemistry Letters, 2007, vol. 36, # 9, p. 1128 - 1129

5
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Reference： [1] Chemistry Letters, 2007, vol. 36, # 9, p. 1128 - 1129

6
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Reference： [1] Patent: EP1189859, 2004, B1, . Location in patent: Page 9

7
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[ 4547-43-7 ]
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Reference： [1] Patent: WO2004/46072, 2004, A1, . Location in patent: Page/Page column 9-10

8
[ 67-56-1 ]
[ 64-18-6 ]
[ 110-94-1 ]
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[ 4547-43-7 ]
[ 1119-40-0 ]
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Reference： [1] Patent: WO2006/48170, 2006, A1, . Location in patent: Page/Page column 13

9
[ 67-56-1 ]
[ 123775-25-7 ]
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[ 1119-40-0 ]
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[ 64037-75-8 ]
[ 106-65-0 ]

Reference： [1] Chemische Berichte, 1990, vol. 123, # 2, p. 391 - 397

10
[ 186581-53-3 ]
[ 112-63-0 ]
[ 553-90-2 ]
[ 627-93-0 ]
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[ 106-65-0 ]

Reference： [1] Monatshefte fuer Chemie, 1991, vol. 122, # 8, p. 719 - 724

11
[ 67-56-1 ]
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[ 627-93-0 ]
[ 4547-43-7 ]
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[ 14273-92-8 ]
[ 931-17-9 ]
[ 106-65-0 ]

Reference： [1] Patent: WO2004/26798, 2004, A2, . Location in patent: Page/Page column 10

12
[ 106-65-0 ]
[ 74-88-4 ]
[ 6138-26-7 ]

Reference： [1] Tetrahedron Letters, 2004, vol. 45, # 22, p. 4405 - 4409

13
[ 106-65-0 ]
[ 6289-46-9 ]

Reference： [1] Helvetica Chimica Acta, 1995, vol. 78, # 6, p. 1525 - 1540
[2] Patent: DE965403, 1957, ,
[3] Patent: US2803644, 1955, ,
[4] Justus Liebigs Annalen der Chemie, 1885, vol. 229, p. 65,76
[5] Patent: CN104276953, 2016, B, . Location in patent: Paragraph 0021
[6] Patent: CN106986771, 2017, A,

14
[ 124-41-4 ]
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Yield	Reaction Conditions	Operation in experiment
75.4%	at 100℃; for 6 h; Inert atmosphere	In a 1 L three-necked flask equipped with an electrically heated magnetic stirrer, a thermocouple, a constant pressure dropping funnel, and a condenser Pressure distillation unit). In a three-necked flask, 600g of dimethyl succinate DMS (4mol), nitrogen (moisture and oxygen removed) Under the care of warming to 100 . Afterwards, 180g of 30percent sodium methylate solution (1mol) was slowly added dropwise with a constant pressure dropping funnel, and the dropping time was about 4h. After the dropping was completed, the reaction was continued for about 2h. After completion of the reaction, the product was obtained, pickled, washed with water and dried to obtain 86 gA yellowish material, dimethyl succinate succinate DMSS, yield 75.4percent,

Reference： [1] Patent: CN106831763, 2017, A, . Location in patent: Paragraph 0027; 0031; 0035

15
[ 67-56-1 ]
[ 124-41-4 ]
[ 106-65-0 ]
[ 6289-46-9 ]

Reference： [1] Patent: WO2018/160618, 2018, A1, . Location in patent: Paragraph 00124

16
[ 79-20-9 ]
[ 106-65-0 ]
[ 6289-46-9 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1914, vol. 404, p. 299

[ 106-65-0 ] Synthesis Path-Downstream 1~87

1
[ 67-56-1 ]
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[ 106-65-0 ]

Yield	Reaction Conditions	Operation in experiment
99.6%	With cyclohexane; at 60 - 80℃;	1. The succinic acid and methanol according to 1 : (3-6) in the molar ratio of reaction kettle heating dissolved, to be completely dissolved is added mole of succinic acid 10-30% cyclonexane the dehydrating agent, catalyst in 60-80 C to dehydration, esterification, liquid during the esterification alcohol-water separation to be implemented in the system, water enters the waste water treatment system, an alcohol esterification with compensation within the system, circulating the dehydrating agent.2. The esterification time the metering control, controls the water outlet section 1-2 hours of the total amount of necessary to achieve 60 , paragraph 2-4 hours of the total amount of the 85 , paragraph 3-6 hours reach of the total amount of more than 96 .3. According to the temperature in the esterification process can be acid value change and esterification progress, 60 C conversion rate reaches the 60 , 70 C conversion reaches 85 , 80 C the conversion is 96 .5. Esterification completed row high-vacuum conditions to extract the obtained with 99.6% product of the above, the control temperature 140-170C, vacuum -0.086 MPa.
97%	With alumina methanesulfonic acid; at 80℃; for 0.133333h;Microwave irradiation;	General procedure: In a typical reaction, AMA 2:3 (332 g, 0.6 mol), the corresponding carboxylicacid (1 mol), and alcohol (1.5-2 mol) were mixed in the provided reaction glass tubeequipped with a screw cap and magnetic agitation until a wet mixture was achieved.The reaction mixture was irradiated with microwaves (Anton Parr Monowave 300reactor) at 80 C for 8 min or 120 C for 20 min. On cooling, the mixture was diluted with dichloromethane (41 mL), filtered under gravity, and washed with dichloromethane;then the filtrate was washed with Na2CO3 (ss) and water. The organic layerwas dried over Na2SO4, filtered, and concentrated under reduced pressure to give theester.
91.1%	With hydrogen; In 1,4-dioxane; methanol; at 200℃; under 60006.0 Torr; for 20h;Inert atmosphere; Autoclave;	Liquid-phase hydrogenation of succinic acid (SA) to 1,4-butanediol (BDO) was carried out over Re/XCu-MC catalysts(X =80, 12.7, 15.9, 23.3, and 26.8) in a batch reactorat 200 C and 80 bar (H2). Succinic acid (0.5 g), methanol(25 ml), and a reduced catalyst (0.2 g) were charged intoan autoclave (150 ml). 1,4-Dioxane (25 ml) was used asa solvent for the reaction. The reactor was purged withnitrogen to remove air, and it was then pressurized up to40 bar using hydrogen. After heating the reactor to reactiontemperature (200 C), hydrogen pressure was raisedup to 80 bar. The catalytic reaction was carried out for20 h. The reaction mixture was stirred at 700 rpm in orderto avoid mass transfer limitation. Reaction products wereanalyzed using a gas chromatograph (Younglin, ACME-6100) equipped with a FID (flame ionization detector).

29.2%	With Amberlyst36; at 60 - 80℃;Large scale;	Example 1 : A vessel was charged with 400 g of succinic acid and 1085 g of methanol. The mixture was heated to 60C and the solution was transferred via HPLC pump into a heating loop where it was heated to 80C and from there into a 60 ml plug flow reactor, equipped with Amberlyst36 catalyst. The mass flow was determined as 122 g/h. Samples, taken at the outlet of the reactor, determined a molar DMS : MMS : SA ratio of 87.5 : 12.0 : 0.5. The composition of the outlet flow was determined as 29.2 wt-% DMS, 3.6 wt-% MMS, 0.1 wt-% SA. 59.5 wt-% MeOH and 7.7 wt-% of water.
	With acidic cation exchange resin Amberlyst 70; at 50 - 160℃;Flow reactor; Green chemistry;	General procedure: Hexanedioic acid and methanol at a weight ratio of 1:5 were mixed at 50 C., and then introduced into the lower part of the vertical reactor at a liquid hourly space velocity (LHSV) of 6 hour-1. The reaction was performed at 130 to 175 C., as shown in Table 2. The reaction was performed at 115 C.. The esterized mixture was output from the upper part of the vertical reactor, and collected to be analyzed by gas photography. The acid value of the product was determined by titration, and the conversion rate and the selectivity were analyzed. The results were shown in Table 2.
	With para-dodecylbenzenesulfonic acid; In chloroform; water; at 65℃; for 20h;	The reaction of succinic acid with methanol in the presence of DBSA was investigated in a biphasic 3-component system (methanol, H2O/organic solvent). The organic solvents used here were chloroform (CHCl3), methyl tert-butyl ether (MTBE) and toluene, which are inert under the reaction conditions. The reaction mixture with MTBE does not form a biphasic mixture under the reaction conditions. GC analysis showed that the esterification in this system proceeds very slowly (Table 2, run 5). The two other solvents, CHCl3 and toluene, form an aqueous phase (methanol/H2O) and an organic phase (methanol/organic solvent). More than 50% yield was already found in both mixtures after seven hours (Table 2, runs 1 to 2). The esterification product was distributed between the two phases. The GC yields of product, which were calculated from the concentrations of dimethyl succinate (DMS) in organic and aqueous phases, are summarized in Table 2. The product distribution between organic and aqueous medium was better in chloroform than in toluene. The free acid and monomethyl succinate (MMS) were also effectively extracted into the organic phase. Toluene was distinctly more selective and dissolves practically no succinic acid and MMS. The best yield of 78% was achieved after 20 hours at 65 C. using CHCl3 and DBSA as catalyst (run 3). The use of other Brnsted acids, namely Amberlyst 15 and sulfuric acid, was likewise investigated. Both catalysts were able to catalyze the esterification. In the case of the strongly acidic cation resin Amberlyst 15, a 3-phase system forms consisting of resin/org. phase/aqueous phase, and therefore the yields are highly dependent on the stirring efficiency (runs 6-9). The use of sulfuric acid is likewise possible (runs 10-11). Here, the acid remained practically exclusively in the aqueous phase.
	at 56 - 95℃; for 5h;Inert atmosphere; Sonication;	Preparation method of high-purity dimethyl succinate succinate,Includes the following steps:1) Add succinic acid to the vessel, stir and heat to 56 C, then raise the temperature to 95 C under nitrogen protection,Excess methanol was added dropwise to the system, the dropping time was 5 hours, and then excess methanol was distilled off under normal pressure, and the product was collected by distillation under reduced pressure to obtain dimethyl succinate

Reference： [1]Patent: CN105367416,2016,A .Location in patent: Paragraph 0017; 0018; 0019; 0020; 0021
[2]Synthetic Communications,2014,vol. 44,p. 2386 - 2392
[3]Journal of Nanoscience and Nanotechnology,2014,vol. 14,p. 8867 - 8872
[4]Patent: WO2014/99431,2014,A1 .Location in patent: Page/Page column 19
[5]Patent: US2017/44086,2017,A1 .Location in patent: Paragraph 0053; 0055
[6]Patent: WO2014/70415,2014,A1 .Location in patent: Page/Page column 9
[7]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 691
[8]Cuihua Xuebao/Chinese Journal of Catalysis,2011,vol. 32,p. 440 - 445
[9]Journal of Organic Chemistry,1983,vol. 48,p. 3106 - 3108
[10]Patent: WO2014/180871,2014,A1 .Location in patent: Page/Page column 9
[11]Journal of the Chemical Society,1948,p. 631
[12]Proceedings of the Indiana Academy of Science,1937,vol. 46,p. 115
Chemisches Zentralblatt,1938,vol. 109,p. 4018
[13]Tetrahedron,1983,vol. 39,p. 1475 - 1485
[14]Green Chemistry,2011,vol. 13,p. 2543 - 2548
[15]Patent: US2013/303796,2013,A1 .Location in patent: Paragraph 0027; 0028; 0034
[16]Patent: US2016/311748,2016,A1 .Location in patent: Paragraph 0074-0081
[17]New Journal of Chemistry,2018,vol. 42,p. 12745 - 12753
[18]Patent: CN109824511,2019,A .Location in patent: Paragraph 0018-0020; 0023-0025

2
[ 109-94-4 ]
[ 106-65-0 ]
[ 58026-12-3 ]

Yield	Reaction Conditions	Operation in experiment
72.3%	With sodium; In diethyl ether; at 40℃; for 5h;	Ethyl formate (71.4 g, 965 mmol) and <strong>[106-65-0]dimethyl succinate</strong> (100 g, 575 mmol) were slowly added to a suspension of metallic sodium (16 g, 690 mmol) in diethyl ether (400 mL) with stirring.After the reaction was carried out at 40 C. for 5 hours, water was carefully added to the reaction solution to terminate the reaction. The obtained mixture was washed with diethyl ether (400 mL × 2), then the aqueous layer was acidified with 6N hydrochloric acid, and the aqueous layer was extracted with diethyl ether (400 mL × 2).The diethyl ether layer was dried over anhydrous sodium sulfate, and the filtrate was concentrated under reduced pressure to obtain dimethyl 2-formyl succinate (Compound 2-1) (100 g, 72.3%) as a yellow solid.
	With sodium methylate; In diethyl ether; at 0 - 20℃;	Synthesis of 5-Methoxycarbonylmethyl-2-thiouracil (181): A mixture of sodium methoxide (13.5 g, 0.25 mol) in 200 mL of diethyl ether was cooled to 0 00 and it was added slowly to a stirred mixture of<strong>[106-65-0]dimethyl succinate</strong> 178 (36.5 g, 0.25 mol) and ethyl formate (18.5 g, 0.25 mol). The reaction mixture was stirred at 0 CC for 3 h, and at room temperature overnight. The solvent was evaporated, and the residue was washed thoroughly with petroleum ether resulting intermediate 180. The crude intermediate 180 was dissolved in methanol, and 19 g (0.25 mol) of thiourea was added. The reaction mixture was refluxed overnight. It was filtered, and the solid was washed with methanol. The filtrate was concentrated underreduced pressure. Flash chromatographic purification on a silica gel column resulting in the desired product 181 in 20% yield.
	With sodium methylate; In diethyl ether; at 0 - 20℃;	Synthesis of 5-Methoxycarbonylmethyl-2-thiouracil (181): A mixture of sodium methoxide (13.5 g, 0.25 mol) in 200 mL of diethyl ether was cooled to 0 C, and it was added slowly to a stirred mixture of <strong>[106-65-0]dimethyl succinate</strong> 178 (36.5 g, 0.25 mol) and ethyl formate (18.5 g, 0.25 mol). The reaction mixture was stirred at 0 C for 3 h, and at room temperature overnight. The solvent was evaporated, and the residue was washed thoroughly with petroleum ether resulting intermediate 180. The crude intermediate 180 was dissolved in methanol, and 19 g (0.25 mol) of thiourea was added. The reaction mixture was refluxed overnight. It was filtered, and the solid was washed with methanol. The filtrate was concentrated under reduced pressure. Flash chromatographic purification on a silica gel column resulting in the desired product 181 in 20% yield.

Reference： [1]Patent: JP2018/168083,2018,A .Location in patent: Paragraph 0091-0092
[2]Patent: US2745845,1950,
[3]Patent: WO2015/196130,2015,A2 .Location in patent: Page/Page column 631
[4]Patent: EP2918275,2015,A1 .Location in patent: Paragraph 2204; 2205

3
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[ 106-65-0 ]
[ 58026-12-3 ]

Yield	Reaction Conditions	Operation in experiment
93.8%	With sodium methylate; In toluene; at 20℃; for 20h;	In a dry 10L four-necked flask, 1800 ml of toluene and 324 g of sodium methoxide were added, and the solution was completely stirred under mild heat.Cool down to below 20 C, and add dropwise a mixture of 730.7 g of <strong>[106-65-0]dimethyl succinate</strong> and 360.3 g of methyl formate.After completion of the dropwise addition, the reaction was stirred for 18 h at room temperature until the material disappeared (GC monitoring). After the reaction was completed, the temperature was lowered to below 10 C., ice water was added to 2 kg, and the mixture was stirred for 20 min to completely dissolve the solution. The toluene layer was extracted twice with water and each time. 300ml, combined water layer;The aqueous layer was adjusted to pH 2-3 with concentrated hydrochloric acid, stirred for 20 minutes until the pH was stable, the oil and water were separated, the aqueous layer was extracted three times with ethyl acetate, and the organic layers were combined.The mixture was washed with saturated brine and the organic layer was concentrated under reduced pressure to recover ethyl acetate to give 816.8 g of a yellow transparent liquid with a yield of 93.8%.
	With sodium methylate; In hydrogenchloride;	EXAMPLE 86 Synthesis of methyl alpha-formylsuccinate This procedure is a modification of published method (Fissekis et al., Biochemistry, 1970, 9, 3136). Sodium methoxide (40.5 g, 0.75 mol) was suspended in dry ether (500 mL) and stirred under nitrogen at 0 C. A mixture of dimethylsuccinate (65.4 mL, 0.5 mol) and methylformate (123 mL, 2 mol) was added dropwise over 30 minutes. The reaction mixture was stirred at 0 C. for 2 h and then at room temperature overnight. Subsequently, the reaction mixture was evaporated to a viscous brown residue which was washed once with petroleum ether and then dissolved in 3 M hydrochloric acid (160 mL). This solution was made weakly acidic with concentrated hydrochloric acid and then extracted with dichloromethane (4*250 mL). The organic phase was dried (MgSO4), filtered and evaporated under reduced pressure. The resulting residue was distilled in a kugelrohr apparatus at 60 C. and 0.6 mBar yielding 52.3 g of a mixture of the title compound and <strong>[106-65-0]dimethyl succinate</strong> in the molar ratio 80:20 (determined by NMR) as a colorless oil. The product is purified of the <strong>[106-65-0]dimethyl succinate</strong> by continuous extraction with diethyl ether. Alternatively the mixture can be used directly for the next step. 1H NMR (DMSO-d6, TMS) delta: 3.2 (s, 2H, CH2), 3.59 (s, 3H, OMe), 3.61 (s, 3H, OMe), 7.73 (s, 1H, CHOH), 10.86 (br s, 1H, CHOH). 13C NMR (DMSO-d6, TMS) ppm: 28.9 (CH2), 51.0 (OMe), 51.6 (OMe), 102.1 (C=CHOH), 156.6 (CHOH), 168.3 (COO), 171.7 (COO).
	With sodium methylate; In hydrogenchloride;	EXAMPLE 26 Methyl alpha-formylsuccinate, FIG. 1(26a) In a modification of the procedure of Fissekis and Sweet, Biochemistry 1970, 9, 3136-42, sodium methoxide (40.5 g, 0.75 mol) was suspended in dry ether (500 ml) and stirred under nitrogen at 0 C. A mixture of dimethylsuccinate (65.4 m, 0.50 mol) and methylformate (123 ml, 2.00 mol) was added dropwise over 30 min. The reaction mixture was stirred at 0 C. for 2 hours and then at room temperature overnight. Subsequently, the reaction mixture was evaporated to a viscous brown residue which was washed once with petroleum ether and then dissolved in 3 M hydrochloric acid (160 ml). This suction was made weakly acidic with concentrated hydrochloric acid and then extracted with dichloromethane (4*250 ml). The organic phase was dried (MgSO4), filtered and evaporated under reduced pressure. The resulting residue was distilled in a kugelrohr apparatus at 60 C. and 0.6 mbar yielding 52.3 g of a mixture of the title compound and <strong>[106-65-0]dimethyl succinate</strong> in the molar ratio 80:20 (determined by NMR) as a colorless oil. This mixture can be used directly in the following preparation. The product can be isolated free of <strong>[106-65-0]dimethyl succinate</strong> by exchanging the extraction with dichloromethane with a continuous extraction with diethyl ether. However, in our hands this reduced the yield to 34%. Fissekis and Sweet, ibid, had reported a 62% yield. 1H-NMR (DMSO-d6/TMS): delta=3.20 (s, 2H, CH2); 3.59 (s, 3H, OMe); 3.61 (s, 3H, OMe); 7.73 (s, 1H, CHOH); 10.86 (br s, 1H, CHOH). 13C-NMR (DMSO-d6/TMS): delta=28.9 (CH2); 51.0 (OMe); 51.6 (OMe); 102.1 (C=CHOH); 156.6 (CHOH); 168.3 (COO); 171.7 (COO).

	With sodium methylate; In hydrogenchloride;	EXAMPLE 26 Methyl alpha-Formylsuccinate, FIG. 1(26a) In a modification of the procedure of Fissekis and Sweet, Biochemistry 1970, 9, 3136-42, sodium methoxide (40.5 g, 0.75 mol) was suspended in dry ether (500 ml) and stirred under nitrogen at 0 C. A mixture of dimethylsuccinate (65.4 ml, 0.50 mol) and methylformate (123 ml, 2.00 mol) was added dropwise over 30 min. The reaction mixture was stirred at 0 C. for 2 hours and then at room temperature overnight. Subsequently, the reaction mixture was evaporated to a viscous brown residue which was washed once with petroleum ether and then dissolved in 3 M hydrochloric acid (160 ml). This solution was made weakly acidic with concentrated hydrochloric acid and then extracted with dichloromethane (4*250 ml). The organic phase was dried (MgSO4), filtered and evaporated under reduced pressure. The resulting residue was distilled in a kugelrohr apparatus at 60 C. and 0.6 mBar yielding 52.3 g of a mixture of the title compound and <strong>[106-65-0]dimethyl succinate</strong> in the molar ratio 80:20 (determined by NMR) as a colorless oil. This mixture can be used directly in the following preparation. The product can be isolated free of <strong>[106-65-0]dimethyl succinate</strong> by exchanging the extraction with dichloromethane with a continuous extraction with diethyl ether. However, in our hands this reduced the yield to 34%. Fissekis and Sweet, ibid, had reported a 62% yield. 1H-NMR (DMSO-d6/TMS): delta=3.20 (s, 2H, CH2); 3.59 (s, 3H, OMe); 3.61 (s, 3H, OMe); 7.73 (s, 1H, CHOH); 10.86 (br s, 1H, CHOH). 13C-NMR (DMSO-d6/TMS): delta=28.9 (CH2); 51.0 (OMe); 51.6 (OMe); 102.1 (C=CHOH); 156.6 (CHOH); 168.3 (COO); 171.7 (COO).
	With sodium methylate; In hydrogenchloride;	EXAMPLE 11 Methyl alpha-formylsuccinate In a modification of the procedure of Fissekis and Sweet, Biochemistry 1970, 9, 3136-42, sodium methoxide (40.5 g, 0.75 mol) was suspended in dry ether (500 mL) and stirred under nitrogen at 0 C. A mixture of dimethylsuccinate (65.4 mL, 0.50 mol) and methylformate (123 mL, 2.00 mol) was added dropwise over 30 minutes. The reaction mixture was stirred at 0 C. for 2 hours and then at room temperature overnight. Subsequently, the reaction mixture was evaporated to a viscous brown residue which was washed once with petroleum ether and then dissolved in 3 M hydrochloric acid (160 mL). This solution was made weakly acidic with concentrated hydrochloric acid and then extracted with dichloromethane (4*250 mL). The organic phase was dried (MgSO4), filtered and evaporated under reduced pressure. The resulting residue was distilled in a kugelrohr apparatus at 60 C. and 0.6 mBar yielding 52.3 g of a mixture of the title compound and <strong>[106-65-0]dimethyl succinate</strong> in the molar ratio 80:20 (determined by NMR) as a colorless oil. This mixture can be used directly in the following preparation. The product can be isolated free of <strong>[106-65-0]dimethyl succinate</strong> by exchanging the extraction with dichloromethane with a continuous extraction with diethyl ether. However, in our hands this reduced the yield to 34%. Fissekis and Sweet,ibid, had reported a 62% yield. 1H-NMR (DMSO-d6/TMS): delta=3.20 (s, 2H, CH2); 3.59 (s, 3H, OMe); 3.61 (s, 3H, OMe); 7.73 (s, 1H, CHOH); 10.86 (br s, 1H, CHOH). 13C-NMR (DMSO-d6/TMS): delta=28.9 (CH2); 51.0 (OMe); 51.6 (OMe); 102.1 (C=CHOH); 156.6 (CHOH); 168.3 (COO); 171.7 (COO).
	With sodium methylate; In hydrogenchloride;	EXAMPLE 84 Synthesis of methyl alpha-formylsuccinate. This procedure is a modification of published method (Fissekis et al., Biochemistry, 1970, 9, 3136). Sodium methoxide (40.5 g, 0.75 mol) was suspended in dry ether (500 mL) and stirred under nitrogen at 0 C. A mixture of dimethylsuccinate (65.4 mL, 0.5 mol) and methylformate (123 mL, 2 mol) was added dropwise over 30 minutes. The reaction mixture was stirred at 0 C. for 2 h and then at room temperature overnight. Subsequently, the reaction mixture was evaporated to a viscous brown residue which was washed once with petroleum ether and then dissolved in 3M hydrochloric acid (160 mL). This solution was made weakly acidic with concentrated hydrochloric acid and then extracted with dichloromethane (4*250 mL). The organic phase was dried (MgSO4), filtered and evaporated under reduced pressure. The resulting residue was distilled in a kugelrohr apparatus at 60 C. and 0.6 mBar yielding 52.3 g of a mixture of the title compound and <strong>[106-65-0]dimethyl succinate</strong> in the molar ratio 80:20 (determined by NMR) as a colorless oil. The product is purified of the <strong>[106-65-0]dimethyl succinate</strong> by continuous extraction with diethyl ether. Alternatively the mixture can be used directly for the next step. 1 H NMR (DMSO-d6, TMS) delta:3.2 (s, 2H, CH2), 3.59 (s, 3H, OMe), 3.61 (s, 3H, OMe), 7.73 (s, 1H, CHOH), 10.86 (br s, 1H, CHOH). 13 C NMR (DMSO-d6, TMS) ppm: 28.9 (CH2), 51.0 (OMe), 51.6 (OMe), 102.1 (C=CHOH), 156.6 (CHOH), 168.3 (COO), 171.7 (COO).
	With sodium methylate; In hydrogenchloride;	EXAMPLE 84 Synthesis of methyl alpha-formylsuccinate This procedure is a modification of published method (Fissekis et al,, Biochemistry, 1970, 9, 3136). Sodium methoxide (40.5 g, 0.75 mol) was suspended in dry ether (500 mL) and stirred under nitrogen at 0 C. A mixture of dimethylsuccinate (65.4 mL, 0.5 mol) and methylformate (123 mL, 2 mol) was added dropwise over 30 minutes. The reaction mixture was stirred at 0 C. for 2 h and then at room temperature overnight. Subsequently, the reaction mixture was evaporated to a viscous brown residue which was washed once with petroleum ether and then dissolved in 3M hydrochloric acid (160 mL). This solution was made weakly acidic with concentrated hydrochloric acid and then extracted with dichloromethane (4*250 mL). The organic phase was dried (MgSO4), filtered and evaporated under reduced pressure. The resulting residue was distilled in a kugelrohr apparatus at 60 C. and 0.6 mBar yielding 52.3 g of a mixture of the title compound and <strong>[106-65-0]dimethyl succinate</strong> in the molar ratio 80:20 (determined by NMR) as a colorless oil. The product is purified of the <strong>[106-65-0]dimethyl succinate</strong> by continuous extraction with diethyl ether. Alternatively the mixture can be used directly for the next step. 1 H NMR (DMSO-d6, TMS) delta:3.2 (s, 2H, CH2), 3.59 (s, 3H, OMe), 3.61 (s, 3H, OMe), 7.73 (s, 1H, CHOH), 10.86 (br s, 1H, CHOH). 13 C NMR (DMSO-d6, TMS) ppm: 28.9 (CH2), 51.0 (OMe), 51.6 (OMe), 102.1 (C=CHOH), 156.6 (CHOH), 168.3 (COO), 171.7 (COO).
	With sodium methylate; In hydrogenchloride;	EXAMPLE 84 Synthesis of Methyl alpha-formylsuccinate This procedure is a modification of published method (Fissekis et al., Biochemistry, 1970, 9, 3136). Sodium methoxide (40.5 g, 0.75 mol) was suspended in dry ether (500 mL) and stirred under nitrogen at 0 C. A mixture of dimethylsuccinate (65.4 mL, 0.5 mol) and methylformate (123 mL, 2 mol) was added dropwise over 30 minutes. The reaction mixture was stirred at 0 C. for 2 h and then at room temperature overnight. Subsequently, the reaction mixture was evaporated to a viscous brown residue which was washed once with petroleum ether and then dissolved in 3 M hydrochloric acid (160 mL). This solution was made weakly acidic with concentrated hydrochloric acid and then extracted with dichloromethane (4*250 mL). The organic phase was dried (MgSO4), filtered and evaporated under reduced pressure. The resulting residue was distilled in a kugelrohr apparatus at 60 C. and 0.6 mBar yielding 52.3 g of a mixture of the title compound and <strong>[106-65-0]dimethyl succinate</strong> in the molar ratio 80:20 (determined by NMR) as a colorless oil. The product is purified of the <strong>[106-65-0]dimethyl succinate</strong> by continuous extraction with diethyl ether. Alternatively the mixture can be used directly for the next step. 1H NMR (DMSO-d6, TMS) delta: 3.2 (s, 2H, CH2), 3.59 (s, 3H, OMe), 3.61 (s, 3H, OMe), 7.73 (s, 1H, CHOH), 10.86 (br s, 1H, CHOH). 13C NMR (DMSO-d6, TMS) ppm: 28.9 (CH2), 51.0 (OMe), 51.6 (OMe), 102.1 (C=CHOH), 156.6 (CHOH), 168.3 (COO), 171.7 (COO).
	With sodium methylate; In hydrogenchloride;	EXAMPLE 11 Methyl alpha-formylsuccinate In a modification of the procedure of Fissekis and Sweet, Biochemistry 1970, 9, 3136-42, sodium methoxide (40.5 g, 0.75 mol) was suspended in dry ether (500 mL) and stirred under nitrogen at 0 C. A mixture of dimethylsuccinate (65.4 mL, 0.50 mol) and methylformate (123 mL, 2.00 mol) was added dropwise over 30 minutes. The reaction mixture was stirred at 0 C. for 2 hours and then at room temperature overnight. Subsequently, the reaction mixture was evaporated to a viscous brown residue which was washed once with petroleum ether and then dissolved in 3 M hydrochloric acid (160 mL). This solution was made weakly acidic with concentrated hydrochloric acid and then extracted with dichloromethane (4*250 mL). The organic phase was dried (MgSO4), filtered and evaporated under reduced pressure. The resulting residue was distilled in a kugelrohr apparatus at 60 C. and 0.6 mBar yielding 52.3 g of a mixture of the title compound and <strong>[106-65-0]dimethyl succinate</strong> in the molar ratio 80:20 (determined by NMR) as a colorless oil. This mixture can be used directly in the following preparation. The product can be isolated free of <strong>[106-65-0]dimethyl succinate</strong> by exchanging the extraction with dichloromethane with a continuous extraction with diethyl ether. However, in our hands this reduced the yield to 34%. Fissekis and Sweet,ibid, had reported a 62% yield. 3H-NMR (DMSO-d4/TMS): delta=3.20 (s, 2H, CH2); 3.59 (s, 3H, OMe); 3.61 (s, 3H, OMe); 7.73 (s, 1H, CHOH); 10.86 (br s, 1H, CHOH). 13C-NMR (DMSO-d4/TMS): delta=28.9 (CH2); 51.0 (OMe); 51.6 (OMe); 102.1 (C=CHOH); 156.6 (CHOH); 168.3 (COO); 171.7 (COO).

Reference： [1]Patent: CN103709126,2018,B .Location in patent: Paragraph 0037; 0038; 0039
[2]Journal fur praktische Chemie (Leipzig 1954),1895,vol. <2> 51,p. 144
[3]Justus Liebigs Annalen der Chemie,1908,vol. 363,p. 358
[4]Patent: US6414112,2002,B1
[5]Patent: US6441130,2002,B1
[6]Patent: US6451968,2002,B1
[7]Patent: US6300318,2001,B1
[8]Patent: US5714331,1998,A
[9]Patent: US5719262,1998,A
[10]Patent: US6710164,2004,B1
[11]Patent: US6734161,2004,B1

4
[ 79-20-9 ]
[ 106-65-0 ]
[ 6289-46-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1914,vol. 404,p. 299

5
[ 2700-47-2 ]
[ 106-65-0 ]
[1-(6-methoxy-[2]naphthyl)-propyl]-succinic acid-1-methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1950,vol. 72,p. 5654,5657

6
[ 20637-08-5 ]
[ 106-65-0 ]
[ 34105-27-6 ]

Reference： [1]Journal of the American Chemical Society,1957,vol. 79,p. 1995,2003

7
[ 1847-68-3 ]
[ 106-65-0 ]
[ 93653-12-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride
	With potassium <i>tert</i>-butylate

Reference： [1]Turner [Journal of the American Chemical Society, 1951, vol. 73, p. 1284,1285] Johnson et al. [Journal of the American Chemical Society, 1957, vol. 79, p. 1995,2003]
[2]Turner [Journal of the American Chemical Society, 1951, vol. 73, p. 1284,1285] Johnson et al. [Journal of the American Chemical Society, 1957, vol. 79, p. 1995,2003]

8
[ 1847-68-3 ]
[ 106-65-0 ]
[ 4423-01-2 ]

Yield	Reaction Conditions	Operation in experiment
	ueber mehrere Stufen;

Reference： [1]Turner [Journal of the American Chemical Society, 1951, vol. 73, p. 1284,1285]

9
[ 106-65-0 ]
[ 110-63-4 ]

Yield	Reaction Conditions	Operation in experiment
97%	With C24H38Cl2N3PRu; hydrogen; sodium methylate; In isopropyl alcohol; at 25℃; under 37503.8 Torr; for 6h;	General procedure: Hydrogenation of Other Ester Compounds Catalyzed by Synthetic Preparation of Bipyridine Tetradshed Ruthenium Complex 5 The results are shown in Table 2:Table 2 Hydrogenation of other ester compounds a; A Reaction conditions: S / C = 1000,3.0 mmol Substrate, 3.0 mumol 5, 3.0 mL lPrOH, 0.3 mmol NaOMe, 5 MPa H2, 25 C.
	With hydrogen;C40H39BN2P2Ru; In tetrahydrofuran; at 80℃; under 37503.8 Torr; for 16h;Product distribution / selectivity;	Example 15 Hydrogenation of Dimethyl Succinate <strong>[106-65-0]Dimethyl succinate</strong> (8 mmol), a ruthenium complex 1 (0.016 mmol), and tetrahydrofuran (3.2 mL) were charged into a 100-mL autoclave equipped with a stirrer. Then, the mixture was subjected to hydrogenation at a hydrogen pressure of 5 MPa at 80 C. for 16 hours. The reaction liquid was analyzed by gas chromatography. As a result, 1.4-butanediol was obtained at a conversion rate of 50% and a selectivity of 71%.
	With hydrogen; at 230℃; under 41254.1 Torr;	According to the process shown in Figure 1 <strong>[106-65-0]dimethyl succinate</strong> hydrogenation.The reaction conditions for controlling the pre-hydrogenation catalyst bed are:Pressure 5.5MPa, temperature 190 , space velocity 0.8h-1,Hydrogen and <strong>[106-65-0]dimethyl succinate</strong> volume ratio of 800: 1. The reaction conditions for controlling the main hydrogenation catalyst bed are:Pressure 5.5MPa, temperature 230 , volume airspeed 0.8h-1,The volume ratio of hydrogen to the reaction mass from the prehydrogenation catalyst bed is 900: 1.The reaction conditions for controlling the replenishment of the refined catalyst bed are:Pressure 5.5MPa, temperature 220 ,The space velocity 4.0 h-1,Dissolved hydrogen and reaction volume from the hot high-grade tank volume ratio of 9: 1.The conversion of <strong>[106-65-0]dimethyl succinate</strong> obtained in this example,The selectivity and purity index of 1,4-butanediol are shown in Table 1.

Reference： [1]Green Chemistry,2014,vol. 16,p. 4081 - 4085
[2]Advanced Synthesis and Catalysis,2016,vol. 358,p. 820 - 825
[3]Patent: CN103980317,2017,B .Location in patent: Paragraph 0098; 0099; 0100; 0101; 0104
[4]Organic Process Research and Development,2012,vol. 16,p. 166 - 171
[5]Journal of the American Chemical Society,2014,vol. 136,p. 7869 - 7872
[6]Patent: US2863928,1956,
[7]Patent: US2010/63294,2010,A1 .Location in patent: Page/Page column 15
[8]Green Chemistry,2011,vol. 13,p. 2543 - 2548
[9]Organic Letters,2015,vol. 17,p. 454 - 457
[10]Journal of the American Chemical Society,2014,vol. 136,p. 13217 - 13225
[11]Angewandte Chemie - International Edition,2016,vol. 55,p. 15364 - 15368
Angew. Chem.,2016,p. 15590 - 15594,5
[12]Chemistry - A European Journal,2018,vol. 24,p. 1046 - 1052
[13]Patent: CN105820038,2016,A .Location in patent: Paragraph 0036-0071; 0079

10
[ 106-65-0 ]
[ 110-14-5 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; ammonia; water

Reference： [1]Morrell [Journal of the Chemical Society, 1914, vol. 105, p. 2704]

11
[ 106-65-0 ]
[ 6289-46-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In methanol; for 4h;Inert atmosphere; Reflux;	The preparation of succinic acid succinic acid diester from succinic acid diester is described in detail with the preparation of dimethyl succinate from dimethyl succinate as an example: , 73 g of dimethyl succinate was added and the mixture was heated to reflux with stirring. A solution of sodium methoxide in methanol (containing 5.4 g of sodium methoxide) was added dropwise to the system under nitrogen. Reflux was continued for 4 h and then cooled. Methanol was added to the system to precipitate a large amount of precipitate, which was filtered off and washed with anhydrous methanol to give a pale yellow solid. The resulting solid was subjected to 4 NMR and 13C NMR (as shown in Figure 2).
	With sodium methylate; In methanol; at 120℃; for 0.916667h;Inert atmosphere;	2) taking the dimethyl succinate solution after the reaction,Stirring under nitrogen protection,Heat to 120 C for 30 min,Then, a sodium methoxide solution is added dropwise thereto under ultrasonic vibration conditions.After the addition is completed,Reflow reaction for another 25 minutes,The reaction is then cooled,Add anhydrous methanol,Stirring,Filtering,And washing the filter cake with anhydrous methanol,The mother liquor and the washing liquid are combined and fractionated.Recovery of methanol and dimethyl succinate;3) After the filter cake is drained,Neutralize with a 20% aqueous solution of sulfuric acid,Precipitating products,Put it at a temperature of 45 C,Dry at reduced pressure for 0.5 h at a pressure of 0.5 atm.That is, a finished product of dimethyl succinyl succinate is obtained.

Reference： [1]Helvetica Chimica Acta,1995,vol. 78,p. 1525 - 1540
[2]Patent: DE965403,1957,
[3]Justus Liebigs Annalen der Chemie,1885,vol. 229,p. 65,76
[4]Patent: CN104276953,2016,B .Location in patent: Paragraph 0021
[5]Patent: CN106986771,2017,A
[6]Patent: CN109824511,2019,A .Location in patent: Paragraph 0018; 0021-0024; 0026-0028

12
[ 106-65-0 ]
[ 4146-43-4 ]

Reference： [1]Synthesis,1993,p. 287 - 289
[2]Angewandte Chemie - International Edition,2013,vol. 52,p. 956 - 959
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 12913 - 12918
Angew. Chem.,2017,vol. 129,p. 13093 - 13098,6
[4]Journal of the American Chemical Society,1964,vol. 86,p. 437 - 440
[5]Journal of general chemistry of the USSR,1964,vol. 34,p. 341 - 344
Zhurnal Obshchei Khimii,1964,vol. 34,p. 343 - 347
[6]Journal of Materials Chemistry B,2016,vol. 4,p. 852 - 858

13
[ 186581-53-3 ]
[ 112-63-0 ]
[ 553-90-2 ]
[ 627-93-0 ]
[ 1732-10-1 ]
[ 1119-40-0 ]
[ 1732-09-8 ]
[ 106-65-0 ]

Reference： [1]Monatshefte fur Chemie,1991,vol. 122,p. 719 - 724

14
[ 908094-01-9 ]
Grahamimycin A₁ [ No CAS ]
[ 1487-49-6 ]
[ 19870-59-8 ]
[ 106-65-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; periodic acid 1.) water:methanol 1:1; 1 h; overnight; 2.) dil. HCl; Multistep reaction;
	With hydrogenchloride; sodium hydroxide; periodic acid 1.) water:methanol 1:1; 1 h; overnight; 2.) dil. HCl; Multistep reaction;

Reference： [1]Ronald, Robert C.; Gurusiddaiah S. [Tetrahedron Letters, 1980, vol. 21, p. 681 - 684]
[2]Ronald, Robert C.; Gurusiddaiah S. [Tetrahedron Letters, 1980, vol. 21, p. 681 - 684]

15
[ 6832-16-2 ]
[ 67-63-0 ]
[ 79-20-9 ]
[ 17639-73-5 ]
[ 17640-21-0 ]
[ 6149-45-7 ]
[ 17639-74-6 ]
[ 106-65-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1980,p. 1636 - 1641

16
[ 6832-16-2 ]
[ 67-63-0 ]
[ 79-20-9 ]
[ 17639-73-5 ]
[ 6149-45-7 ]
[ 106-65-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1980,p. 1636 - 1641
[2]Journal of the Chemical Society. Perkin transactions II,1980,p. 1636 - 1641

17
[ 67-56-1 ]
[ 123775-25-7 ]
[ 13984-50-4 ]
[ 1119-40-0 ]
[ 76700-85-1 ]
[ 64037-75-8 ]
[ 106-65-0 ]

Reference： [1]Chemische Berichte,1990,vol. 123,p. 391 - 397

18
[ 6933-25-1 ]
[ 106-65-0 ]
[ 81541-44-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol for 1h;

Reference： [1]Moussa; Abdel-Meguid [Journal of Heterocyclic Chemistry, 1981, vol. 18, # 8, p. 1519 - 1522]

19
[ 952-92-1 ]
[ 624-48-6 ]
(7-Benzyl-1,3-dioxo-1,2,3,7-tetrahydro-[2,7]naphthyridin-4-yl)-acetic acid methyl ester [ No CAS ]
[ 106-65-0 ]
[ 67146-57-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 19 % Turnov. 2: 14 % Turnov.	With tris(2,2'-bipyridyl)ruthenium dichloride In methanol Irradiation; Yields of byproduct given;

Reference： [1]Pac,C.; Ihama,M.; Yasuda,M. [Journal of the American Chemical Society, 1981, vol. 103, p. 6495]

20
[ 952-92-1 ]
[ 624-49-7 ]
(7-Benzyl-1,3-dioxo-1,2,3,7-tetrahydro-[2,7]naphthyridin-4-yl)-acetic acid methyl ester [ No CAS ]
[ 106-65-0 ]
[ 67146-57-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 21 % Turnov. 2: 29%	With tris(2,2'-bipyridyl)ruthenium dichloride In methanol Irradiation; Yields of byproduct given;

Reference： [1]Pac,C.; Ihama,M.; Yasuda,M. [Journal of the American Chemical Society, 1981, vol. 103, p. 6495]

21
[ 952-92-1 ]
[ 106-65-0 ]
[ 67146-57-0 ]

Yield	Reaction Conditions	Operation in experiment
35 % Turnov.	With tris(2,2'-bipyridyl)ruthenium dichloride; C₆H₈O₄ In pyridine; methanol Irradiation; Yields of byproduct given;

Reference： [1]Pac,C.; Ihama,M.; Yasuda,M. [Journal of the American Chemical Society, 1981, vol. 103, p. 6495]

23
[ 67-56-1 ]
[ 74-85-1 ]
[ 144-62-7 ]
[ 553-90-2 ]
[ 627-93-0 ]
[ 1732-09-8 ]
[ 106-65-0 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1980,vol. 29,p. 259 - 262
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1980,p. 344 - 348

24
[ 67-56-1 ]
[ 74-85-1 ]
[ 144-62-7 ]
[ 553-90-2 ]
[ 627-93-0 ]
[ 1732-09-8 ]
[ 106-79-6 ]
[ 106-65-0 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1980,vol. 29,p. 259 - 262
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1980,p. 344 - 348

25
[ 67-56-1 ]
[ 144-62-7 ]
[ 553-90-2 ]
[ 627-93-0 ]
[ 1732-09-8 ]
[ 106-65-0 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1980,vol. 29,p. 259 - 262
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1980,p. 344 - 348

26
[ 74-97-5 ]
[ 624-48-6 ]
[ 826-34-6 ]
[ 826-35-7 ]
[ 106-65-0 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 1592 - 1597

27
[ 624-48-6 ]
[ 74-95-3 ]
[ 826-34-6 ]
[ 826-35-7 ]
[ 106-65-0 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 1592 - 1597
[2]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 1592 - 1597

28
[ 624-49-7 ]
[ 74-95-3 ]
[ 826-35-7 ]
[ 106-65-0 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 1592 - 1597

29
[ 119-61-9 ]
[ 106-65-0 ]
[ 23242-84-4 ]

Yield	Reaction Conditions	Operation in experiment
~ 100%	With potassium tert-butylate; In toluene; for 2.5h;Heating / reflux;	Potassium t-butoxide (75 grams, 0.67 mole) was added to a reaction flask containing 200 milliliters (mL) of toluene. The reaction flask was equiped with an overhead stirrer, dropping funnel, and a condenser with nitrogen inlet. The contents of the reaction flask was heated to reflux temperature and a mixture of benzophenone (91 grams, 0.5 mole), <strong>[106-65-0]dimethyl succinate</strong> (90 grams, 0.62 mole), and toluene (100 grams) was added over a period of one-half hour. The resulting pasty mixture was refluxed an additional two hours, cooled, and about 400 mL of water was added and mixed well. The aqueous layer was separated, acidified with dilute hydrochloric acid, and extracted with 200 mL of toluene. The solvents, toluene and residual t-butanol, were removed on the rotary evaporator to produce a near quantitative yield of crude Stobbe half-ester: 4,4-diphenyl-3-methoxycarbonyl-3-butenoic acid. This material was not purified further but was used directly in the next step.

Reference： [1]Patent: EP906366,2003,B1 .Location in patent: Page 12
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. 20,p. 362 - 365
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1999,vol. 38,p. 488 - 490
[4]Patent: EP906366,2003,B1 .Location in patent: Page 11

30
[ 4925-88-6 ]
[ 106-65-0 ]
[ 97944-74-6 ]

Reference： [1]Australian Journal of Chemistry,1985,vol. 38,p. 777 - 792

31
[ 4925-88-6 ]
[ 106-65-0 ]
[ 83441-15-0 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1982,p. 686 - 688

32
[ 5417-17-4 ]
[ 106-65-0 ]
[ 103346-93-6 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1615 - 1627

33
[ 100-46-9 ]
[ 106-65-0 ]
[ 2142-06-5 ]
[ 149142-51-8 ]

Reference： [1]Tetrahedron,1995,vol. 51,p. 1495 - 1502

34
[ 106-65-0 ]
[ 53171-39-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With ammonia In 1,4-dioxane at 30℃; for 31h;

Reference： [1]Puertas, Susana; Rebolledo, Francisca; Gotor, Vicente [Tetrahedron, 1995, vol. 51, # 5, p. 1495 - 1502]

35
[ 3294-60-8 ]
[ 106-65-0 ]
[ 14203-24-8 ]

Reference： [1]Chemische Berichte,1977,vol. 110,p. 3118 - 3125

36
[ 100-52-7 ]
[ 106-65-0 ]
[ 125702-14-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium tert-butylate; In N,N-dimethyl-formamide; at 20℃; for 2h;	To a stirring solution of benzaldehyde (500 mg, 4.7 mmol) and <strong>[106-65-0]dimethyl succinate</strong> (732 mg, 4.7 mmol) in DMF (4 mL) was added potassium fert-butoxide (369 mg, 4.7 mmol) and the mixture was stirred at room temperature for 2 hours. After that, the reaction mixture was diluted with water (30 mL) and extracted by EtOAc (2 x 30 mL). The combined organic layers were washed by brine (50 mL) and dried over anhydrous sodium sulphate. After removal of EtOAc, (E)-3- (methoxycarbonyl)-4-phenylbut-3-enoic acid was obtained as yellow oil without further purification (1.0 g, yield: 97%).

Reference： [1]Synthesis,2000,p. 154 - 164
[2]Patent: WO2013/83991,2013,A1 .Location in patent: Page/Page column 110-111
[3]European Journal of Organic Chemistry,2007,p. 758 - 767
[4]Advanced Synthesis and Catalysis,2008,vol. 350,p. 85 - 94
[5]Advanced Synthesis and Catalysis,2008,vol. 350,p. 76 - 84
[6]Tetrahedron,2010,vol. 66,p. 7198 - 7203
[7]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2566 - 2570

37
[ 162147-12-8 ]
[ 106-65-0 ]
2-[1-(2-Bromo-5-isopropoxy-phenyl)-meth-(Z)-ylidene]-succinic acid 1-methyl ester [ No CAS ]
2-[1-(2-Bromo-5-isopropoxy-phenyl)-meth-(E)-ylidene]-succinic acid 1-methyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2000,p. 799 - 811

38
isophorone oxide [ No CAS ]
[ 106-65-0 ]
[ 74-88-4 ]
[ 6138-26-7 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 4405 - 4409

39
[ 760-90-7 ]
[ 106-65-0 ]

Reference： [1]Journal of Organic Chemistry,1983,vol. 48,p. 1114 - 1116

40
[ 253801-04-6 ]
[ 106-65-0 ]
C₁₃H₁₂N₂O₄ [ No CAS ]
C₁₃H₁₂N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tert-butyl alcohol; at 60℃; for 2h;	Intermediate Product 2: methyl 2-[1-(1H-indazol-5-yl)-methylidene]-succinate; 3.40 g (29.69 mmol) potassium-tert-butoxide was added to a solution of 2.00 g (13.68 mmol) 1H-indazol-5-carbaldehyde and 2.80 mL (20.97 mmol) dimethyl succinate in 100 mL tert-butanol and the mixture was stirred for 2 h at 60 C. The reaction mixture was cooled to RT, diluted with 200 mL water and the aqueous phase was washed twice with EtOAc. The aqueous phase was acidified with semiconc. aqueous HCl to pH 3-4 and exhaustively extracted with EtOAc. The combined org. phases were dried over magnesium sulphate, filtered through activated charcoal and evaporated down i. vac. The crude product was triturated with diisopropylether and a little isopropanol, filtered off and the residue was washed with diisopropylether (3.60 g, 1st stereoisomer). The mother liquor was evaporated down i. vac. and the residue was purified by column chromatography (silica gel, EtOAc/HOAc 10/0.1 v/v) and dried i. vac. (3.60 g, 2nd stereoisomer). Yield: 7.20 g (2 stereoisomers, 74% of theory) Rf=0.49 (silica gel, EtOAc/HOAc 100/1 v/v) ESI-MS: (M+H)+=261

Reference： [1]Patent: US2005/227968,2005,A1 .Location in patent: Page/Page column 16

41
[ 253801-04-6 ]
[ 106-65-0 ]
[ 635713-14-3 ]

Reference： [1]Patent: WO2005/84672,2005,A1 .Location in patent: Page/Page column 41
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2912 - 2916

42
[ 67-56-1 ]
[ 64-18-6 ]
[ 110-94-1 ]
[ 124-04-9 ]
[ 1191-25-9 ]
[ 13392-69-3 ]
[ 556-48-9 ]
[ 542-28-9 ]
[ 627-93-0 ]
[ 4547-43-7 ]
[ 1119-40-0 ]
[ 14273-92-8 ]
[ 931-17-9 ]
[ 106-65-0 ]

Reference： [1]Patent: WO2004/26798,2004,A2 .Location in patent: Page/Page column 10

43
[ 627-93-0 ]
[ 1119-40-0 ]
[ 23235-61-2 ]
[ 106-65-0 ]
[ 67-56-1 ]

Yield	Reaction Conditions	Operation in experiment
	With di(n-butyl)tin oxide at 5 - 10℃; Heating / reflux;	7.i EXAMPLE 7; [0075] Step (i): 800 g of Estasol (mixed dibasic ester comprising 21%-w/w of dimethyladipate, 59%-w/w of dimethylglutarate and 20%-w/w of dimethylsuccinate), 309.5 g of di(trimethylolpropane), 3.3 g dibutyltinoxide and 2.2 g of trisnonylphenylphosphite were charged in a reaction flask equipped with electrical heating, a Dean-Starkseparator, a vertical cooler, mechanical stirrer and nitrogen inlet. The temperature was under stirring and nitrogen blanket raised until all di(trimethylolpropane) was dissolved and formed methanol progressively distilled off. The temperature was allowed to decrease 5-10[deg.] C. during the alcoholysis. The alcoholysis was considered completed when 160 ml of methanol was collected and unreacted Estasol was distilled off from formed di(trimethylolpropane) ester. [0076] Step (ii): 200 g of the di(trimethylolpropane) ester obtained in Step (i), 111 g of diethanolamine and 0.3 g dibutyltinoxide were charged in a reaction flask equipped as in Step (i). The temperature slowly raised to 220[deg.] C. and methanol removed from the reaction mixture. The aminolysis was considered completed when 34 ml of methanol was collected. Vacuum was now applied to remove unreacted diethanolamine and obtained [beta]-hydroxyamide was recovered. [0077] Obtained [beta]-hydroxyamide had a hydroxyl value of 7.62 mequiv/g and a viscosity of 428 mPas at 100[deg.] C.

Reference： [1]Current Patent Assignee: PERSTORP HOLDING AB - US2003/195373, 2003, A1 Location in patent: Page/Page column 5

44
[ 627-93-0 ]
[ 1119-40-0 ]
[ 126-58-9 ]
[ 106-65-0 ]
[ 67-56-1 ]

Yield	Reaction Conditions	Operation in experiment
	With di(n-butyl)tin oxide; at 165 - 185℃;Product distribution / selectivity;	EXAMPLE 2; [0060] Step (i): 800 g of Estasol (mixed dibasic ester comprising 21%-w/w of dimethyladipate, 59%-w/w of dimethylglutarate and 20%-w/w of dimethylsuccinate), 193 g of dipentaerythritol, 3 g dibutyltinoxide and 2 g of trisnonylphenylphosphite were charged in a reaction flask equipped with electrical heating, a Dean-Stark separator, a vertical cooler, mechanical stirrer and nitrogen inlet. The temperature was under stirring and nitrogen blanket raised to 170[deg.] C. and formed methanol progressively distilled off. The temperature was maintained at 170[deg.] C. and the alcoholysis was considered completed when 140 ml of methanol was collected. Vacuum was applied and excess of Estasol was evaporated from formed dipentaerythritol ester. [0061] Step (ii): 200 g of the dipentaerythritol ester obtained in Step (i), 124 g of diethanolamine and 0.3 g dibutyltinoxide were charged in a reaction flask equipped as in Step (i). The temperature slowly raised to 220[deg.] C. and methanol removed from the reaction mixture. The aminolysis was considered completed when 37 ml of methanol was collected. Vacuum was now applied to remove unreacted diethanolamine and obtained [beta]-hydroxyamide was recovered.[0062] Obtained [beta]-hydroxyamide had a hydroxyl value of 8.23 mequiv/g and a viscosity of 740 mPas at 100[deg.] C.; EXAMPLE 3; [0063] Step (i): 500 g of Estasol (mixed dibasic ester comprising 21%-w/w of dimethyladipate, 59%-w/w of dimethylglutarate and 20%-w/w of dimethylsuccinate), 106.5 g of pentaerythritol, 1.8 g dibutyltinoxide and 1.2 g of trisnonylphenylphosphite were charged in a reaction flask equipped with electrical heating, a Dean-Stark separator, a vertical cooler, mechanical stirrer and nitrogen inlet. The temperature was under stirring and nitrogen blanket raised to 185[deg.] C. and formed methanol progressively distilled off. The temperature was allowed to decrease to 165[deg.] C. during the alcoholysis and the alcoholysis was considered completed when 100 ml of methanol was collected and unreacted Estasol was distilled off from formed pentaerythritol ester. [0064] Step (ii): 200 g of the pentaerythritol ester obtained in Step (i), 130 g of diethanolamine and 0.3 g dibutyltinoxide were charged in a reaction flask equipped as in Step (i). The temperature slowly raised to 220[deg.] C. and methanol removed from the reaction mixture. The aminolysis was considered completed when 39 ml of methanol was collected. Vacuum was now applied to remove unreacted diethanolamine and obtained [beta]-hydroxyamide was recovered. [0065] Obtained [beta]-hydroxyamide had a hydroxyl value of 8.52 mequiv/g and a viscosity of 660 mPas at 100[deg.] C.

Reference： [1]Patent: US2003/195373,2003,A1 .Location in patent: Page/Page column 4

45
[ 67-56-1 ]
[ 64-18-6 ]
[ 110-94-1 ]
[ 124-04-9 ]
[ 1191-25-9 ]
[ 13392-69-3 ]
[ 556-48-9 ]
[ 627-93-0 ]
[ 4547-43-7 ]
[ 1119-40-0 ]
[ 14273-92-8 ]
[ 931-17-9 ]
[ 106-65-0 ]

Reference： [1]Patent: WO2006/48170,2006,A1 .Location in patent: Page/Page column 13

46
[ 936716-42-6 ]
[ 3153-37-5 ]
[ 106-65-0 ]
[ 1085783-84-1 ]

Yield	Reaction Conditions	Operation in experiment
	at 125℃; for 4h;	To a solution of 4-amino-2-{4-[2-(trifluoromethyl)phenoxy]piperidin-l-yl}-l,3- thiazole-5-carboxamide (245 mg, 0.63 mmol, from Step 4 of Example 1) in dimethyl succinate (1 mL) was added dropwise carbomethoxypropionyl chloride (0.15 mL, 1.2 mmol). The resulting yellow solution was stirred at 125 0C for 4 h. The reaction mixture was allowed to cool to rt and partitioned between EtOAc and aqueous ammonium. acetate (25 % w/v). The organic layer was dried over Na2SO4 and concentrated. The crude product was loaded onto silica gel and eluted with a gradient of ethyl acetate in hexanes going from 80 % to 100 % to afford the title compound as a white solid. 1H NMR (400 MHz, J6-acetone): delta 11.15 (bs, IH), 7.68-7.61 (m, 2 H), 7.39 (d, 1 H), 7.15-7.10 (m, 1 H), 5.08-5.04 (m, 1 H), 3.88-3.80 (m, 4 H), 3.65 (s, 3 H), 3.06-3.02 (t, 2 H), 2.91-2.89 (t, 2 H), 2.23-2.15 (m, 2 H), 2.07-1.98 (m, 2 H) ppm. MS (APCI, Q+) m/z 483.2 [M+H]+.

Reference： [1]Patent: WO2008/141455,2008,A1 .Location in patent: Page/Page column 40

47
[ 52289-54-0 ]
[ 77-78-1 ]
[ 106-65-0 ]
[ 634197-32-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-methoxysalicylaldehyde; Dimethyl succinate With sodium methylate In methanol for 2h; Heating / reflux; Stage #2: dimethyl sulfate With potassium carbonate In acetone for 2.5h; Heating / reflux;	31.b Further steps (steps b-d) were carried out with some modification of a related procedure (31). To a stirred solution of the aldehyde 60 (1.50 g; 10.0 mmol) and dimethyl succinate (1.49 mL; 11.4 mmol) in methanol (26 mL) was added a solution of sodium methoxide (3.3 mL; 10.5 mmol; 3.2 M in methanol). The reaction mixture was heated under reflux for 2 hours before cooling to room temperature. The reaction volume was reduced by half under reduced pressure and the remaining solution was cooled in ice and acidified with 6 M HCl and then diluted with water (100 mL). The product was extracted into chloroform (200 mL) and the extract was dried (MgS04) and evaporated to give an orange oil. Flash chromatography (ethyl acetate/hexane, 25: 75) afforded the monoester as a viscous oil (419 mg). This was dissolved in acetone (15 mL) and treated with anhydrous [K2CO3] (543 mg; 3.93 mmol) and dimethyl sulfate (373 [1L] ; 3.93 mmol). The whole was heated under reflux for 2.5 hours before cooling to room temperature and quenching with saturated ammonium chloride solution. The product was extracted into dichloromethane (3 x 50 mL) and the combined extracts were washed with 25% ammonia solution and dried (MgSO4). Evaporation of the solvent gave the diester 61 as a yellow oil (485 mg). This was used in the next step without purification.

Reference： [1]Current Patent Assignee: CORTICAL - WO2003/104178, 2003, A1 Location in patent: Page 91-92

48
[ 23055-10-9 ]
[ 106-65-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With palladium on activated charcoal; hydrogen; at 165℃; under 45004.5 Torr;	Example 1In this example 1 only the first reactor was used. A stream of liquid DMM was fed to the first reactor with Palladium on carbon catalyst, under the following conditions: Pressure: 60 bargTemperature: 100 to 165 CMolar ratio H2/DMM: 50Liquid hourly Space Velocity: about 2The main results of tests at different temperatures are shown in Table 2Table 2 - DMM Hydrogenation to DMSThis example 1 shows the catalyst for the first step of reaction has both the necessary characteristics: i) high selectivity to the saturation of the carbon double bond and very low selectivity to the hydrogenolysis , ii) high activity to the saturation of the carbon double bond even at moderate temperature.Even if, due to the small size of the laboratory equipment, the fully adiabatic conditions were not reproduced, a computer simulation of the conditions used during the test showed the increment of temperature from the inlet to the outlet of an adiabatic fixed bed reactor is around 60 C.

Reference： [1]Patent: WO2013/76747,2013,A1 .Location in patent: Page/Page column 25; 26
[2]Applied Organometallic Chemistry,2011,vol. 25,p. 1 - 8
[3]Tetrahedron Letters,2010,vol. 51,p. 4250 - 4252
[4]Ultrasonics Sonochemistry,2010,vol. 17,p. 26 - 29

49
[ 51234-09-4 ]
[ 106-65-0 ]
[ 1160440-49-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 20℃;	1.2 EXAMPLE 1.2Preparation of 4,6,7-trimethoxy-8-methyl-2-naphthoic acid (Compound 4)4,6,7-Trimethoxy-8-methyl-2-naphthoic acid (7) is prepared in six steps according to the following reaction diagram. Reduction of 3,4-dimethoxy-2-methylbenzoic acid (1) to aldehyde (2) can be carried out by the Rosenmund reaction (SOCl2 then H2, Pd/BaSO4) (see reference 27). The aldehyde (2) is then reacted with dimethyl succinate (Stobbe reaction) (see reference 28). The coupling product (3) is not isolated but is treated directly with sodium acetate in the presence of acetic anhydride and acetic acid (AcOH/Ac2O 1:1) to give 4. After saponification, 4-hydroxy-6,7-dimethoxy-8-methyl-2-naphthoic acid (5) is obtained with a yield of 70% (3 steps). After esterification under the conditions described above (90%), compound 6 is hydrolysed to give 4,6,7-trimethoxy-8-methyl-2-naphthoic acid (7) (92%).

Reference： [1]Current Patent Assignee: UNIVERSITY OF MAINE LE MANS - US2010/331398, 2010, A1 Location in patent: Page/Page column 14

50
[ 617-90-3 ]
[ 18908-66-2 ]
[ 106-65-0 ]
[ 1286755-28-9 ]

Yield	Reaction Conditions	Operation in experiment
25%	Stage #1: 2-furancarbonitrile; Dimethyl succinate With tert-Amyl alcohol; sodium at 120℃; for 1.83333h; Inert atmosphere; Stage #2: In N,N-dimethyl-formamide at 120℃; for 0.5h; Inert atmosphere; Stage #3: 3-bromomethylheptane In N,N-dimethyl-formamide at 140℃; for 6h; Inert atmosphere;

Reference： [1]Woo, Claire H.; Beaujuge, Pierre M.; Holcombe, Thomas W.; Lee, Olivia P.; Frechet, Jean M. J. [Journal of the American Chemical Society, 2010, vol. 132, # 44, p. 15547 - 15549]

51
[ 1003-31-2 ]
[ 106-65-0 ]
3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With iron(III) chloride; sodium tert-pentoxide; at 145℃; for 2.5h;	Tert-amylalcohol (50 mL), sodium (1.00 g, 43.50 mmol), and catalytic amount of ferricchloride (5 mg) were added to a three-neck round-bottom flask. The mixture washeated at 145 C under reflux until sodium was completely dissolved.Thiophene-2-carbonitrile (1.40 mL, 15.03 mmol) was added and dimethyl succinate(0,92 mL, 7,03 mmol) was added dropwise during 30 minutes. The reaction mixturewas further heated at 145 C under reflux for 2 hours, cooled to 25 C, whereuponmethanol (40 mL) and hydrochloric acid (5 mL, 35%) were added. The resulting darkred precipitate was filtered off and washed with methanol several times.
88.2%	With potassium tert-butylate; In tert-Amyl alcohol; at 90 - 110℃;Inert atmosphere;	In two 500ml round bottom flask was added potassium t-butoxide (20.00g, 180mmol), <strong>[1003-31-2]2-cyanothiophene</strong> (16.40g, 150.0mmol), 125ml of tert-amyl alcohol, N2 protection. At 90 deg.] C was slowly added dropwise dimethyl succinate (7.3g, 50.0mmol) and reacted overnight at 100-110 C. Cooling to 65 C, glacial acetic acid was added dropwise until the move is not swept modulation Woo, diluted with methanol, stirred at 70 C, 20min, washed with water, washed with methanol, to give a dark red solid (13.22 g, 88.2% yield).
88.2%	With potassium tert-butylate; In tert-Amyl alcohol; at 90 - 110℃;Inert atmosphere;	In a 500 ml two-neck round bottom flask,Potassium tert-butoxide (20.00 g, 180 mmol) was added.2-cyanopyrene (16.40g, 150.0mmol),125 ml of tert-amyl alcohol, protected by N2.Dimethyl succinate (7.3 g, 50.0 mmol) was slowly added dropwise at 90 C to react at 100-110 C overnight.Cool down to 65 C,Add glacial acetic acid dropwise until it is plucked, dilute with methanol, stir at 70 C for 20 min, wash with water, wash with methanol.A dark red solid (13.22 g, yield 88.2%) was obtained.

87%	With sodium; In pentan-1-ol; for 1.83333h;	A 500 mL three-neck round-bottom flask connectedto a condenser and dry nitrogen flow was charged witha stir bar and tert-amyl alcohol (250 mL). Sodium metal pieces(2.40 g, 107 mmol) were progressively added to thewarmed solution of tert-amyl alcohol (333-343 K).After complete addition of the sodium, the temperaturewas progressively raised to 393 K. The mixture wasstirred overnight at 393 K. Thiophen-2-carbonitrile (1) (10.0 g, 107 mmol) was subsequently added to the hotmixture of sodium alkoxide. Dimethyl succinate (5.23 g,35.8 mmol) was then added drop wise over a period of20 min (the reaction mixture turned dark orange-red),and the resulting mixture was stirred for 1.5 h. The reactionmixture was then cooled to room temperature, andthe precipitated sodium salt 2 was filtered over aBuchner funnel for collection and dried under vacuum(14.7 g, 87 % yield). Compound 2 was used withoutfurther purification.
16.3%	With potassium tert-butylate; In tert-Amyl alcohol; at 110℃; for 3h;	(1) Add 29 g of potassium tert-butoxide to a three-neck round bottom flask, start degassing and then fill with nitrogen,Three consecutive times, then 179 mL of tert-amyl alcohol was added and stirred at 110 C for 2 h.Then 20 mL of 3-cyanothiophene was added dropwise and stirred for 45 min.Using a dropping funnel, 9.4 mL of dimethyl succinate and 29 mL of tert-amyl alcohol solution were added dropwise and stirred.Continue stirring for 3h.After the reaction solution was cooled to 80 C, 108 mL of methanol and 29 mL of deionized water were added and stirred for 45 min. After the solution was cooled to room temperature,Add 57 mL of hydrochloric acid and 287 mL of methanol and stir for 45 min.The treated reaction solution was filtered, and the residue was washed with 72 mL of methanol to obtain compound (I).The mass of the obtained compound was 9.54 g, and the yield was 16.3%;The chemical reaction equation is as follows:
	With sodium tert-pentoxide; In pentan-1-ol; at 110℃; for 5h;Inert atmosphere;	under argon atmosphere,Sodium tert-amylate (2.39 g, 21.7 mmol) and 5 mL of tert-amyl alcohol were added to a 100 mL two-necked flask, and the mixture was stirred at 120 C for 1 hour. After the sodium tert-amylate is completely dissolved,0.91 mL of <strong>[1003-31-2]2-cyanothiophene</strong> (1.09 g, 10 mmol) was added.After the solution became dark, dimethyl succinate (0.57 mL, 4.34 mmol) was slowly added dropwise.The solution quickly turned reddish brown. After heating at 110 C for 5 hours,After cooling to room temperature, diluted with 10 mL of methanol, 1.5 mL of glacial acetic acid was added to quench the reaction, at which time a large amount of dark purple solid precipitated.After cooling to room temperature, suction filtration, washing with anhydrous methanol until the filtrate was colorless.A black red solid was obtained with a crude yield of 75%.

Reference： [1]Beilstein Journal of Organic Chemistry,2017,vol. 13,p. 2374 - 2384
[2]Patent: CN106432283,2017,A .Location in patent: Paragraph 0008; 0010
[3]RSC Advances,2018,vol. 8,p. 25031 - 25039
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[16]Patent: CN110183452,2019,A .Location in patent: Paragraph 0103-0106
[17]Journal of the American Chemical Society,2010,vol. 132,p. 15547 - 15549
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[29]Patent: CN108794490,2018,A .Location in patent: Paragraph 0047; 0048; 0049

52
[ 51234-09-4 ]
[ 106-65-0 ]
C₁₆H₂₀O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.26 g	With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Le, Tin Thanh; Chau, Nguyet Trang Thanh; Nguyen, Tai Tan; Brien, Josselin; Thai, Trieu Tien; Nourry, Arnaud; Castanet, Anne-Sophie; Nguyen, Kim Phi Phung; Mortier, Jacques [Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 601 - 608]

53
[ 5392-10-9 ]
[ 106-65-0 ]
[ 1178511-90-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium <i>tert</i>-butylate In methanol for 48h; Inert atmosphere; Reflux;	5.2.1.1. (E)-4-(2'-bromo-4',5'-dimethoxyphenyl)-3-methoxycarbonyl-3-butenoic acid (12) Dimethyl succinate (775 mg, 5.30 mmol) and 2-bromo-4,5-dimethoxybenzaldehyde refPreviewPlaceHolder[19] S. Chandrasekhar, N.R. Reddy and Y.S. Rao. Tetrahedron, 62 (2006), pp. 12098-12107. [19] (11) (500 mg, 2.04 mmol) were added to a solution of potassium-tert-butoxide (916 mg, 8.16 mmol) in dry methanol (8 mL). The mixture was refluxed for 48 h, then poured into stirred aqueous 10% HCl solution at 0 °C, and extracted with EtOAc (3 × 80 mL). The extract was washed with water (100 mL) and extracted with 0.5 N aqueous NaOH (3 × 50 mL). The aqueous phase was acidified with half-concentrated HCl solution, and extracted with EtOAc (3 × 100 mL). The organic layer was washed with H2O, saturated aqueous NaCl, dried over Na2SO4, and concentrated. The residue was recrystallized from EtOAc to afford 12 as a yellow solid (660 mg, 1.84 mmol, 90%). Mp 148-150 °C (EtOAc). IR (KBr, cm-1) ν 2961, 2836, 2361, 2111, 1717, 1697, 1596, 1502, 1466, 1436, 1387, 1330, 1262, 1206, 1167, 1092, 1023, 920, 871, 814, 770, 745, 607. 1H NMR (CDCl3) δ 3.49 (s, 2H, CH2), 3.87 (s, 3H, OCH3), 3.89 (s, 3H, OCH3), 3.90 (s, 3H, OCH3), 7.04 (s, 1H, CCH), 7.09 (s, 1H, Ar-H), 7.93 (s, 1H, Ar-H), 10.72 (br s, 1H, COOH). 13C NMR (CDCl3) δ 34.5, 53.1, 56.5, 56.5, 113.1, 115.5, 115.8, 124.9, 126.8, 142.9, 148.7, 150.6, 168.9, 173.3. EI-MS (70 eV) m/z (%): 358 (3), 279 (100), 220 (11). MS (ESI) exact mass calcd for C14H16BrO6: 359.01248 [M + H]+; found: 359.01248 [M + H]+.

Reference： [1]Location in patent: experimental part Bringmann, Gerhard; Zhang, Guoliang; Hager, Anastasia; Moos, Michael; Irmer, Andreas; Bargou, Ralf; Chatterjee, Manik [European Journal of Medicinal Chemistry, 2011, vol. 46, # 12, p. 5778 - 5789]

54
[ 79447-10-2 ]
[ 106-65-0 ]
[ 1380855-46-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: [1,1′-biphenyl]-4-yl(3-methoxyphenyl)methanone; Dimethyl succinate With potassium <i>tert</i>-butylate In toluene at 20 - 40℃; Inert atmosphere; Stage #2: With hydrogenchloride; water In toluene	12.2 Step 2; In an oven-dried flask placed under a nitrogen atmosphere, the product of Step 1 (153 g) and potassium iert-butoxide (95.3 g) were stirred in toluene (1850 mL) using a mechanical stirrer. To this was added dimethyl succinate (120 mL) via addition funnel slowly over a 1 hour period of time. The reaction mixture was then heated to 40°C for 2 hours. It was cooled to room temperature and then slowly poured into a beaker containing deionized water (2 L) and ice while stirring vigorously. Concentrated hydrochloric acid was slowly added to the mixture while stirring until pH 1 was reached. A separatory funnel was used to separate the organic and aqueous layers. The aqueous layer was extracted with ethyl acetate (2 x 1 L). The organic layers were combined, washed with deionized water (2 x 1 L), dried over magnesium sulfate and concentrated by rotary evaporation to yield an amber colored oil containing a mixture of (E and Z) 4-([1 , -biphenyl]-4-yl)-3-methoxycarbonyl-4-(3-methoxyphenyl)but-3-enoic acid (260 g) which was used in the next reaction as is.

Reference： [1]Current Patent Assignee: ESSILORLUXOTTICA - WO2012/82999, 2012, A1 Location in patent: Page/Page column 57

55
diazomethylene [ No CAS ]
(2R,3E)-N-[(1S,2S,3R,4E,8Z)-2,3-dihydroxy-1-(hydroxymethyl)-4,8-tetracosadienyl]-2-hydroxy-3-octadecenamide [ No CAS ]
[ 7132-64-1 ]
[ 112-39-0 ]
[ 106-65-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (2R,3E)-N-[(1S,2S,3R,4E,8Z)-2,3-dihydroxy-1-(hydroxymethyl)-4,8-tetracosadienyl]-2-hydroxy-3-octadecenamide With potassium permanganate; sodium periodate; potassium carbonate In water; acetone at 37℃; for 18h; Stage #2: With sulfuric acid In water; acetone Stage #3: diazomethylene In diethyl ether

Reference： [1]Mehmood, Rashad; Bibi, Amna; Malik, Abdul [Turkish Journal of Chemistry, 2013, vol. 37, # 1, p. 111 - 118]

56
[ 624-45-3 ]
[ 108-24-7 ]
[ 553-90-2 ]
[ 89-91-8 ]
[ 106-65-0 ]

Reference： [1]ChemSusChem,2013,vol. 6,p. 2255 - 2258

57
[ 108-31-6 ]
[ 67-56-1 ]
[ 3878-55-5 ]
[ 3052-50-4 ]
[ 106-65-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 32.9 %Chromat. 2: 12.48 %Chromat. 3: 8.07 %Chromat.	With palladium on activated charcoal; hydrogen at 190℃; Autoclave;	3 50g, 0.5 mol maleic anhydride, 49g, 1.53 mol, 3 eqv methanol, 1g, equivalent to 0.32g, 0.6 wt% palladium-carbon paste were charged to the autoclave. The vessel was sealed and then pressurised to 300 psig with hydrogen and heated to 190°C. The internal temperature of the vessel was recorded with time and, to ensure that any exotherm above the desired maximum temperature was monitored, the cooling system was turned off. The results indicated that, although the rate of temperature increase did go up, the temperature did not exceed the maximum operating parameter. Analysis of the product showed significant conversion of the maleate species to succinate with (methanol free) selectivity to mono methyl maleate and mono maleate succinate of 7.28 mol % and 1 1.08 mol % respectively. Selectivity to di-methyl maleate and dimethyl succinate were 3.59 mol% and 26.41 mol% respectively. The results are set out in the following table.

Reference： [1]Current Patent Assignee: JOHNSON MATTHEY PLC - WO2015/55992, 2015, A1 Location in patent: Page/Page column 11; 12

58
[ 15970-74-8 ]
[ 106-65-0 ]
4-(furan-2-yl)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)but-3-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62 g	With potassium <i>tert</i>-butylate In toluene for 1.5h;	3.2 Step 2 The product of Step 1 (80 g), dimethyl succinic ester (115 g) and toluene (800 ml) were placed in a three-neck 3 L flask equipped with a mechanical stirrer. Potassium t-butoxide (67 g) was added in batches over a 30 minute period. An exothermic reaction was observed along with the formation of a large amount of precipitate. After a one hour hold, water (800 mL) was added and the mixture transferred to a separatory funnel. The aqueous phase was collected and washed twice with toluene (200 mL). The pH was adjusted to 2 using 3N HCl, resulting in the separation of a large amount of oil. To the mixture was added ethyl acetate (500 mL). After stirring at ambient temperature for 10 minutes, the organic layer was collected, washed with brine and dried over MgSO4. After concentration, the crude product was purified through a silica gel plug with the use of a gradient of 10/90 to 60/40 ethyl acetate/hexane as the eluent. A viscous oil (95 g) was obtained. 1H NMR showed that the obtained product (62 g) had a structure consistent with 1/1 Z/E mixture of 4-(furan-2-yl)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)but-3-enoic acid.
62 g	With potassium <i>tert</i>-butylate In toluene for 1.5h;	3.2 Example 3 Step 2 [0208] The product of Step 1 (80 g), dimethyl succinic ester (115 g) and toluene (800 ml) were placed in a three-neck 3 L flask equipped with a mechanical stirrer. Potassium t-butoxide (67 g) was added in batches over a 30 minute period. An exothermic reaction was observed along with the formation of a large amount of precipitate. After a one hour hold, water (800 mL) was added and the mixture transferred to a separatory funnel. The aqueous phase was collected and washed twice with toluene (200 mL). The pH was adjusted to 2 using 3N HCl, resulting in the separation of a large amount of oil. To the mixture was added ethyl acetate (500 mL). After stirring at ambient temperature for 10 minutes, the organic layer was collected, washed with brine and dried over MgSO4. After concentration, the crude product was purified through a silica gel plug with the use of a gradient of 10/90 to 60/40 ethyl acetate/hexane as the eluent. A viscous oil (95 g) was obtained. 1H NMR showed that the obtained product (62 g) had a structure consistent with 1/1 Z/E mixture of 4-(furan-2-yl)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)but-3-enoic acid.

Reference： [1]Current Patent Assignee: ESSILORLUXOTTICA - US9029565, 2015, B1 Location in patent: Paragraph 0287
[2]Current Patent Assignee: ESSILORLUXOTTICA - US2015/141662, 2015, A1 Location in patent: Paragraph 0207; 0208

59
[ 1224430-39-0 ]
[ 106-65-0 ]
C₂₆H₃₂N₂O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate In tert-Amyl alcohol

Reference： [1]Guo, Huan; Shen, Tianpei; Wu, Fen; Wang, Guo; Ye, Linglong; Liu, Zhaoxia; Zhao, Bin; Tan, Songting [RSC Advances, 2016, vol. 6, # 16, p. 13177 - 13184]

60
[ 623-00-7 ]
[ 106-65-0 ]
[ 84632-54-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With iron(III) chloride; sodium; In tert-Amyl alcohol; at 90℃; for 25h;Inert atmosphere;	Sodium (1.26 g, 54.74 mmol) and anhydrous FeCl3 (0.06 g) was added to dry 2-methyl-2-butanol (27.2mL) under nitrogen atmosphere and the mixture was stirred at 90 C until all the sodium was dissolved.The reaction mixture was cooled to 90 C, then 4-bromobenzonitrile (4.98 g, 27.37 mmol) was added andagain heated to 90 C. A solution of <strong>[106-65-0]dimethyl succinate</strong> (1.26 g, 10.95 mmol) in dry 2-methyl-2-butanol(8.2 mL) was added dropwise for 1 h. The reaction mixture was heated under nitrogen atmosphere at90 C for 24 h. Acetic acid (11.5 mL) was added to the mixture and stirred at 120 C for 1 h. The reactionmixture was cooled down to room temperature and filtered. The filtered dark red solid was washed withhot water and hot MeOH several times and used for next reaction without further purification. Yield: 5.31g, (60%).

Reference： [1]Heterocycles,2017,vol. 94,p. 1040 - 1054
[2]New Journal of Chemistry,2018,vol. 42,p. 20113 - 20122
[3]Dyes and Pigments,2016,vol. 127,p. 37 - 44

61
[ 100-47-0 ]
[ 106-65-0 ]
[ 54660-00-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: benzonitrile; Dimethyl succinate With potassium <i>tert</i>-butylate In tert-Amyl alcohol at 108℃; for 1h; Inert atmosphere; Stage #2: With acetic acid In methanol; tert-Amyl alcohol at 65℃; for 0.166667h; Inert atmosphere;
	With sodium In tert-Amyl alcohol Reflux;

Reference： [1]Shi, Huaxia; Sun, Wucheng; Wang, Qiang; Gu, Guiying; Si, Weili; Huang, Wei; Zhang, Qi; Dong, Xiaochen [ChemPlusChem, 2016, vol. 81, # 6, p. 515 - 520]
[2]Calvo-Castro, Jesus; Morris, Graeme; Kennedy, Alan R.; McHugh, Callum J. [Crystal Growth and Design, 2016, vol. 16, # 9, p. 5385 - 5393]

62
[ 67-56-1 ]
[ 624-45-3 ]
[ 553-90-2 ]
[ 106-65-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: levulinic acid methyl ester With oxygen; manganese(III) triacetate dihydrate; acetic anhydride at 90℃; for 10h; Stage #2: methanol
	Stage #1: levulinic acid methyl ester With manganese(II) acetate; copper(II) nitrate; acetic acid at 60℃; for 4h; Stage #2: methanol With boron trifluoride diethyl etherate for 4h; Reflux;	1 0.33 g of methyl levulinate, 0.5 mol% (relative to levulinic acid methyl ester) manganese acetate (II) and 0.5 mol% of copper nitrate,Add to the 35mL reaction kettle, add 2mL glacial acetic acid, off the kettle, filled with oxygen pressure of 0.1MPa,Slow up to 60 ° C with stirring and hold for 4 h. Then cooled to room temperature, carefully reduced to atmospheric pressure.The whole product was transferred to a 50 mL round bottom flask, 20 mL of anhydrous methanol and 100 mg of boron trifluoride ether were added, heated under reflux for 4 h,Cooled to room temperature, the liquid all transferred to the 25mL volumetric flask, add 2mL internal standard TMB (are four toluene) after the volume,Gas chromatography retention time using GC-MS and standard materials was characterized by characterization of the major products,And then sampled using gas chromatography (GC, left in Figure 2)The conversion of the raw material and the selectivity of the product succinic acid diester were obtained by internal standard method. The conversion of methyl levulinate was 98.3% and the selectivity of dimethyl succinate was 83.5%.

Reference： [1]Xia, Fei; Du, Zhongtian; Liu, Junxia; Ma, Yangyang; Xu, Jie [RSC Advances, 2016, vol. 6, # 76, p. 72744 - 72749]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Dalian Institute of Chemical Physics (in: CAS) - CN104119224, 2016, B Location in patent: Paragraph 0020; 0023

63
[ 89424-83-9 ]
[ 106-65-0 ]
(E)-3-(methoxycarbonyl)-4-(benzo[d][1,3]dioxol-6-yl)but-3-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; sodium; for 2h;Reflux;	General procedure: A mixture of aldehyde 1(a-c), 66.6 mmol) and dimethylsuccinate (79.6 mmol) in methanol was added to a solutionof NaOMe (100 mmol, prepared by dissolving Na metal indry methanol and followed by removing the excessmethanol) in methanol (100 mL). The mixture was heatedunder reflux for 2 h, cooled and acidified with HCl (2 N).This mixture was then extracted with Et2O (3 × 100 mL).The Et2O fraction was then back-extracted with aq.NaHCO3 (3 × 75 mL). Acidification of the aq. NaHCO3extract with con. HCl provided an oily residue. This residuewas then extracted with CH2Cl2 (3 × 100 mL) and theextract was washed with water (2 × 30 mL), dried overNaSO4 and evaporated to yield a yellow solid. This wasrecrystallized from methanol to get the intermediate compound2(a-c).

Reference： [1]Medicinal Chemistry Research,2016,vol. 25,p. 2906 - 2915

64
[ 89424-83-9 ]
[ 106-65-0 ]
(E)-dimethyl-2-((benzo[d][1,3]dioxol-6-yl)methylene)succinate [ No CAS ]

Reference： [1]Medicinal Chemistry Research,2016,vol. 25,p. 2906 - 2915

65
[ 1868-00-4 ]
[ 106-65-0 ]
4,4-bis(3-trifluoromethylphenyl)-3-methoxycarbonyl-3-butenoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate In toluene at 50 - 70℃; for 4.5h; Inert atmosphere;	1.1 Potassium t-butoxide (26.4 grams) was weighed into a 2 liter reaction flask equipped with a mechanical stirrer, placed under a nitrogen atmosphere and 1200 milliliters (mL) of toluene was added followed by 3,3’-bistrifluoromethylbenzophenone (50 grams). The reaction mixture was stirred mechanically and heated to 50°C. Dimethyl succinate (28.7 grams) was added to the reaction mixture over a 30 minute period. The reaction mixture became viscous and 100 mL of toluene was added to dilute the reaction mixture. The reaction mixture was heated at 70°C for 4 hours. After cooling to room temperature, the reaction mixture was poured into 1000 mL of water and the toluene layer discarded. The aqueous layer was extracted with diethyl ether (2 x 700 mL) to remove the neutral products, and then acidified the aqueous layer with concentrated hydrochloric acid. A yellow oily liquid was obtained from the aqueous layer, and was extracted with 2 x 600 mL of methylene chloride. The organic layers were combined, washed with saturated NaCl solution (1 x 700 mL) and dried over anhydrous sodium sulfate. Removal of the solvent by rotary evaporation yielded 65 grams of a mixture of (E and Z) 4,4-(bis (3-trifluoromethylphenyl))-3-methoxycarbonyl-3-butenoic acid as a brownish yellow oil. This material was not purified further and was used directly in the next step.

Reference： [1]Current Patent Assignee: ESSILORLUXOTTICA - KR101593284, 2016, B1 Location in patent: Paragraph 0107; 0108; 0109

66
[ 67-56-1 ]
[ 1927-25-9 ]
[ 50768-69-9 ]
[ 106-65-0 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: 250 g of DL-homoserine and 250 g of water were placed in a reactor and reacted while injecting NO / O 2 gas at room temperature (25 ° C) and atmospheric pressure (1 atm). The results of the component analysis of the product of the reaction after completion of the reaction are shown in Table 36 below. The product thus obtained was subjected to dehydration cyclization of 2,4-dihydroxy-butanoic acid and esterification of succinic acid in the same manner as in Example 13-2 to give HO-GBL (22.6percent) and DMS (63 percent). The reaction was carried out in the same manner as in Example 13-1, but the product was not separated after direct de-amidation and hydrolysis of O-SH (30 g). First, water was used as a solvent. However, since the solubility of O-SH in water is 8.7 g / L, when O-SH is added in the initial stage of the reaction, NO(N2, Ar, etc.) or nitrogen gas generated through the deamination reaction, bubbles are generated, so that a small amount of the bubbles is injected several times. The amount of O-SH finally added was 250 g, and the concentration was 50 wtpercent based on O-SH. The product was distilled under reduced pressure to remove water and acid, and then 60 g of methanol and 2 g of Conc. H2SO4 was added and the mixture was refluxed for 2 hours to dehydrate and cyclize the 2,4-dihydroxy-butanoic acid, and the succinic acid was esterified to obtain hydroxy-gamma butyrolactone, dimethyl succinate and monomethylsuccinate / RTI & gt; The final product was analyzed by GC and the results are shown in Table 35 below.

Reference： [1]Patent: KR2015/118287,2015,A .Location in patent: Paragraph 0300-0303

67
[ 75-65-0 ]
[ 106-65-0 ]
[ 926-26-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With caesium carbonate; lithium hydroxide at 81 - 83℃; for 24h;	3 Dimethyl succinate (146 g, 1 mol) was added to a 2 L four-necked flask,Tert-butanol (740 g, lOmol) and Li0H / Cs2C03 (7.5 g, where LiOH was lg (0.04 mol)Cs2C03 was 6.5 g (0.02 mol)),The reaction was heated to reflux (81-83 ° C)And in this state to maintain 24 hours,The methanol produced during the continuous distillation through the distillation column (tower efficiency equivalent to 15 theoretical plates)At the same time continue to add fresh t-butanol,The total amount of about 290g.When the top temperature is 76 to 78 ° C,Gas chromatographic analysis showed that,Dimethyl succinate has been fully reacted.The unreacted tert-butyl alcohol was distilled off under reduced pressure,The residue was diluted with 300 ml of toluene and washed with water until neutral,The toluene was distilled off under reduced pressure,The residue was further distilled under reduced pressure,The fraction of l0-10 ° C / 20 mmHg was collected to give 173 g of di-tert-butyl succinate,GC purity 99%, yield 76%.

Reference： [1]Current Patent Assignee: HUBEI DINGLONG CO., LTD.; EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN103804190, 2016, B Location in patent: Paragraph 0033; 0034

68
[ 111-42-2 ]
[ 106-65-0 ]
methyl 4-(bis(2-hydroxyethyl)amino)-4-oxobutanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With pyridine; In toluene; at 150℃; for 28h;	<strong>[106-65-0]Dimethyl succinate</strong> (20.0 g, 136.9 mmol) and dihydroxyethylamine (7.20 g, 68.7 mmol) in the mixture of anhydrous toluene (500 ml) and pyridine (50 ml) were refluxed at 150 C. for 28 h. The mixture was concentrated and purified on Si02 column eluted with EtOAc/DCM (5% 25% EtOAc) to afford the title compound (12.5 g, 83% yield). ESI MS mlz+for C9H17NaNO5 (M+Na) cald 242.2, found 242.4.
83%	With pyridine; In toluene; at 150℃; for 28h;	<strong>[106-65-0]Dimethyl succinate</strong> (20.0 g, 136.9 mmol) and dihydroxyethylamine (7.20 g, 68.7 mmol) in the mixture of anhydrous toluene (500 ml) and pyridine (50 ml) were refluxed at 150 C for 28 h. The mixture was concentrated and purified on Si02 column eluted with EtOAc/DCM (5%-25% EtOAc) to afford the title compound (12.5 g, 83% yield). ESI MS m/z [M + Na] + 242.4.
83%	With pyridine; In toluene; at 150℃; for 28h;	<strong>[106-65-0]Dimethyl succinate</strong> (20.0 g, 136.9 mmol) and dihydroxyethylamine (7.20 g, 68.7 mmol) were dissolved in a mixed solution of anhydrous toluene (500 ml) and pyridine (50 ml) and refluxed at 150 C. for 28 hours. After concentrating the combined solution, purification on SiO 2 column (EtOAc / DCM = 5% -25% to EtOAc) gave the title compound (12.5 g, 83%).

83%

With pyridine; In toluene; at 150℃; for 28h;

<strong>[106-65-0]Dimethyl succinate</strong> (20.0g, 136.9mmol) and dihydroxyethylamine (7.20g, 68.7mmol) were dissolved in a mixed solution of anhydrous toluene (500ml) and pyridine (50ml) and refluxed at 150 C for 28 hours .The mixed solution was concentrated and subjected to SiO2column chromatography (from EtOAc / DCM = 5% -25% to EtOAc) to obtain the title compound (12.5 g, 83%).

Reference： [1]Patent: US2017/157262,2017,A1 .Location in patent: Paragraph 0184; 0185
[2]Patent: WO2017/46658,2017,A1 .Location in patent: Page/Page column 155
[3]Patent: JP2017/160205,2017,A .Location in patent: Paragraph 0203; 0204
[4]Patent: CN110279872,2019,A .Location in patent: Paragraph 0031; 0272-0274

69
[ 110-15-6 ]
[ 359845-21-9 ]
[ 627-73-6 ]
[ 123-25-1 ]
[ 106-65-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 14 %Chromat. 2: 19.1 %Chromat. 3: 50.2 %Chromat.	With carbon dioxide at 150℃; for 18h; Green chemistry;

Reference： [1]Silva, Daniel; Bogel-Lukasik, Ewa [Green Chemistry, 2017, vol. 19, # 17, p. 4048 - 4060]

70
[ 124-41-4 ]
[ 106-65-0 ]
[ 6289-46-9 ]

Yield	Reaction Conditions	Operation in experiment
75.4%	at 100℃; for 6h;Inert atmosphere;	In a 1 L three-necked flask equipped with an electrically heated magnetic stirrer, a thermocouple, a constant pressure dropping funnel, and a condenser Pressure distillation unit). In a three-necked flask, 600g of dimethyl succinate DMS (4mol), nitrogen (moisture and oxygen removed) Under the care of warming to 100 . Afterwards, 180g of 30% sodium methylate solution (1mol) was slowly added dropwise with a constant pressure dropping funnel, and the dropping time was about 4h. After the dropping was completed, the reaction was continued for about 2h. After completion of the reaction, the product was obtained, pickled, washed with water and dried to obtain 86 gA yellowish material, dimethyl succinate succinate DMSS, yield 75.4%,

Reference： [1]Patent: CN106831763,2017,A .Location in patent: Paragraph 0027; 0031; 0035

71
[ 106-65-0 ]
[ 58026-12-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; methanol; at 0 - 25℃; for 12h;	Methanol (122 mg, 3.80 mmol) was added dropwise into a mixture of sodium hydride (2.3 g, 57.50 mmol, 60%) and THF (50 mL) at 0C. To the mixture was added a mixture of methyl formate (15 mL, 244.80 mmol) and 1, 4-dimethyl butanedioate (5 mL, 38.20 mmol) dropwise with stirring at 0C. The resulting solution was stirred for 12 h at 25 C. The resulting mixture was concentrated under vacuum. The pH value of the resulting solution was adjusted to 2 with hydrogen chloride (3M). The resulting solution was extracted with dichloromethane, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column eluting with dichloromethane/ethyl acetate (10/1) to afford the title compound (8 g crude) as yellow oil. LCMS [M+H+] 175.

Reference： [1]Patent: WO2018/96159,2018,A1 .Location in patent: Paragraph 0542-0545

72
[ 67-56-1 ]
[ 124-41-4 ]
[ 106-65-0 ]
[ 6289-46-9 ]

Reference： [1]Patent: WO2018/160618,2018,A1 .Location in patent: Paragraph 00124

73
[ 611-97-2 ]
[ 106-65-0 ]
C₂₀H₂₀O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium <i>tert</i>-butylate In toluene at 110℃; for 4h;	Synthesis of 3-(ethoxycarbonyl)-4,4-di-p-tolylbut-3-enoic acid³¹ (2) A mixture of t-BuOK (8.81 g, 0.07 mol), 4,4′-dimethylbenzophenone (15.00 g, 0.07 mol, purchased from Aladdin), dimethyl succinate (11.50 g, 0.08 mol) and toluene (120 mL) were stirred for 4 h with heating to 110 °C. After completion of the reaction, the mixture was cooled to 40 °C. The crude product was extracted with toluene(3 × 30 mL). The combined organic phases were dried with anhydrous Na2SO4 and concentrated under reduced pressure. The purified product was obtained by recrystallisation from ethyl acetate and n-hexane (5:1) to give compound 2 as a yellow solid; yield 16.86 g (73%); m.p.211-213 °C; 1H NMR (400 MHz, DMSO-d6): δ 12.44 (s, 1H, -COOH),7.14 (d, J = 9.4 Hz, 2H, ArH), 7.04 (d, J = 8.4 Hz, 2H, ArH), 6.90 (d, J= 9.2 Hz, 2H, ArH), 6.82 (d, J = 8.4 Hz, 2H, ArH), 3.53 (s, 5H, -CH2-,-CH3), 2.22 (s, 6H, -CH3); 13C NMR (101 MHz, DMSO-d6): δ 172.5,169.7, 150.6, 139.4, 138.3, 137.6, 129.5, 129.2, 129.1, 128.8, 124.8, 51.7,40.4, 40.2, 21.2. Anal. calcd for C20H20O4: C, 74.06; H, 6.22; found: C,74.08; H, 6.23%.

Reference： [1]Zhao, Qian; Yang, Yanhua; Shen, Kecheng; Tao, Xian; Shen, Yingzhong [Journal of Chemical Research, 2018, vol. 42, # 9, p. 447 - 452]

74
[ 35588-60-4 ]
[ 106-65-0 ]
[ 4187-56-8 ]
[ 27298-99-3 ]
C₁₃H₁₆ClNO₃ [ No CAS ]
C₁₃H₁₆ClNO₃ [ No CAS ]

Reference： [1]Chirality,2018,vol. 30,p. 1225 - 1232

75
[ 4038-14-6 ]
[ 106-65-0 ]
4-(3,4-dimethoxyphenyl)-3-(methoxycarbonyl)-4-phenylbut-3-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium tert-butylate; In toluene; at 110℃; for 34h;	Potassium (3.10 g, 0.08 mol) andt-BuOH (110 ml) were stirred at 60 C for 3 h under nitrogen until the potassium disappeared. t-BuOH was evaporated under reduced pressure to obtain the white solid (t-BuOK). Then <strong>[4038-14-6](3,4-dimethoxyphenyl)(phenyl)methanone</strong> (5) (15.00 g, 0.06 mol), dimethyl succinate (11.50 g, 0.07 mol), and toluene (100 ml) were added and stirred at 110 C for 34 h. After completion of the reaction, water (100 ml) was added, and the aqueous phase was extracted with toluene (3×50 ml). The combined organic phases were dried over anhydrous Na2SO4, concentrated under reduced pressure, and product 6 was purified by recrystallization from n-hexane-EtOAc, 4:1. Yield 18.86 g (85 %), yellow solid,mp 211-212 C. 1H NMR spectrum, delta, ppm (J, Hz): 3.48(3H, d, J = 2.4, OCH3); 3.59 (2H, s, CH2); 3.78 (3H, s,OCH3); 3.89 (3H, s, OCH3); 6.68-6.73 (2H, m, H Ar); 6.83-6.87 (1H, m, H Ar); 7.10-7.14 (2H, m, H Ar); 7.26-7.29 (3H,m, H Ar). 13C NMR spectrum, delta, ppm: 27.4; 38.4; 51.7;55.9; 81.2; 110.9; 112.5; 122.2; 123.4; 127.9; 128.8; 133.8; 141.9; 148.7; 149.3; 152.8; 169.2; 170.2; 177.2. Found, %:C 67.26; H 5.73. C20H20O6. Calculated, %: C 67.41; H 5.66
	In 5,5-dimethyl-1,3-cyclohexadiene; tert-butyl alcohol; for 3h;Reflux;	General procedure: The obtained product a1 in the previousstep, diethyl succinate, xylene and tert-butanol were addedto the reaction flask, heated to reflux for 3 h, until the solution turned to a viscous liquid, the reactionwas monitored.The reaction solution was cooled, stirred for 10 min andallowed to stand for separation. The aqueous layer was separatedinto a reaction flask, toluene was added to adjust thepH to about 2, and the aqueous layer was separated, andthe toluene was distilled under reduced pressure until substantiallyno more produced, and a2 was obtained.

Reference： [1]Chemistry of Heterocyclic Compounds,2018,vol. 54,p. 840 - 847
Khim. Geterotsikl. Soedin.,2018,vol. 54,p. 840 - 847,8
[2]Journal of Biomolecular Structure and Dynamics,2020

76
[ 1228630-89-4 ]
[ 106-65-0 ]
C₁₆H₂₆N₂O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%		First step: Compound 1 (100 g, 434.29 mol) was dissolved in dimethyl sulfoxide (500 mL) and stirred at 25 C.Then tetrabutylammonium iodide (160.41 g, 434.29 mmol) and potassium fluoride (126.15 g, 2.17 mol) were added.After 10 minutes, dimethyl maleate (312.96 g, 2.17 mol, 272.14 mL) was added and the temperature was raised to 40 C for 22 hours.TLC (petroleum ether/ethyl acetate volume ratio = 3/1) showed the reaction was completed.Water (2.5 L) was added to the reaction system, followed by extraction with tert-butyldimethyl ether (500 mL x 5).The organic phase was dried over anhydrous sodium sulfate and evaporatedPetroleum ether / ethyl acetate ~ petroleum ether / ethyl acetate volume ratio = 5:1 ~ 10:1)The yellow oily compound 2 (140.2 g, 374.48 mmol) was obtained in a yield of 86%.

Reference： [1]Patent: CN109651368,2019,A .Location in patent: Paragraph 0006; 0007

77
[ 106-65-0 ]
[ 4100-80-5 ]

Yield	Reaction Conditions	Operation in experiment
	With acetyl chloride for 2h;	5 To a glass flask, 101.2 g (766 mmol) of methyl succinic acid was added, and 400 mL of acetyl chloride was added dropwise. After stirring for 2 hours,Purify by vacuum distillation after concentration,83.6 g of methyl succinic anhydride was obtained.To a glass flask, 26.3 g (705 mmol) of lithium aluminum hydride and 800 mL of tetrahydrofuran were added, and this was dissolved in 200 mL of tetrahydrofuran.41.0 g (359 mmol) of succinic anhydride was added dropwise over 1 hour. After stirring for 2 days, a mixture of 100 mL of tetrahydrofuran and 100 mL of water was added dropwise, and 500 mL of tetrahydrofuran was added to the resulting slurry. After drying with sodium sulfate, the solvent was distilled off. The obtained crude product was distilled to obtain 28.5 g of 2-methyl-1,4-butanediol. *

Reference： [1]Current Patent Assignee: MITSUBISHI CHEMICAL HOLDINGS CORPORATION; Mitsubishi Chemical Corp (in: MCHC Group) - JP2019/172650, 2019, A Location in patent: Paragraph 0058

78
[ 5779-94-2 ]
[ 106-65-0 ]
[ 31318-44-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 2,5-dimethylbenzaldehyde; Dimethyl succinate With sodium hydride In toluene Reflux; Stage #2: With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 24h;	2,5-Dimethylbenzylsuccinic acid (2) To a stirring suspension of NaH (268 mg, 6.71 mmol) in toluene (5 mL), heated at refluxfor 15 min, was added very slowly a mixture of DMS (399 mg, 0.3 mL, 2.73 mmol) and aldehyde 1 (305 mg, 2.28 mmol) dissolved in toluene (10 mL). The mixture was stirred for 20 h at refluxing temperature, cooled, diluted with water and extracted with ether.The aqueous phase was cooled, acidified with aqueous HCl (5%) and extracted with ether. The combined organic extracts were dried and evaporated to obtain amber colored material (380 mg) which was dissolved in EtOH (10 mL), Pd/C (10%, 389 mg)added and the mixture stirred under hydrogen for 24 h. The reaction mixture was filtered and evaporated under reduced pressure to give a solid, which on chromatographic purification (hexane:ether 4:6) afforded the diacid 2 (351 mg, 65%); mp. 140-141 C (lit.2 mp unspecified); IR (cm1): 3407 (OH), 1726 (CO), 1704 (CO); MS (m/z): 105(M- CH2-CH(COOH)-CH2-COOH); 1H NMR (acetone-d6): d 10.65 (bs, 2H, 2-COOH), 7.03 (d, 1H, J 7.65 Hz, H-4’), 6.99 (s, 1H, H-6’), 6.92 (d, 1H, J 7.65 Hz, H-3’), 3.07-3.01 (m, 2H, H-2, H-5), 2.73 (dd, 1H, J 15.50 Hz, 10.50 Hz, H-5), 2.66 (dd,1H, J 17.00 Hz, 9.00 Hz, H-3), 2.40 (dd, 1H, J17.00, 4.50 Hz, H-3), 2.29 (s, 3H, 2’-Me), 2.24 (s, 3H, 5’-Me); 13C NMR (Acetone-d6): d: 175.83 (C-1), 173.30 (C-4), 137.78(C-2’), 135.83 (C-5’), 133.92 (C-1’), 131.38 (C-6’), 131.15 (C-4’), 128.09 (C-3’), 42.52 (C-2), 35.63 (C-5), 35.44 (C-3), 20.93 (2’-Me), 18.93 (5’-Me).Anal. Calcd for C13H16O4: C, 66.08; H, 6.83. Found: C, 66.31; H, 6.99.

Reference： [1]Marrugo, Kelly P.; Maldonado, Alexis; Banerjee, Ajoy K.; Cabrera, Elvia V. [Organic Preparations and Procedures International, 2020, vol. 52, # 5, p. 442 - 445]

79
[ 66739-89-7 ]
[ 106-65-0 ]
3,6-bis[4-(1,3-dioxolan-2-yl)phenyl]pyrrolo[3,4-c]pyrrole-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With iron(III) chloride; sodium In tert-Amyl alcohol at 100℃; for 25h; Inert atmosphere;

Reference： [1]Diao, Yingxue; Ke, Hanzhong; Qin, Xihao; Xu, Nanfeng; Xu, Zhengtao; Zhu, Xunjin [Dalton Transactions, 2020, vol. 49, # 44, p. 15587 - 15591]

80
[ 67-56-1 ]
[ 57-48-7 ]
[ 624-45-3 ]
[ 106-65-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 23% 2: 31%	With oxygen at 130℃; for 4h;	1.2. Typical experiment All the experiments were carried out in a 50 mL stainless steelautoclave supplied by the Anhui Kemi Company equipped with a thermocoupleand magnetic stirrer (800 rpm). Initially, 75 mg of the catalystwas added to 1.5 mmol of the substrate in 15 mL of methanol. Exactly10 bar pressure of O2 was added after purging the reaction thrice. Thereaction mixture was stirred and heated to the desired temperature. Thetarget temperature was achieved after 10-15 min at which point thetime was set to zero. On completion of the reaction, the stirring wasstopped and the autoclave was cooled in the water bath until a temperaturebelow 25C was attained. The residual pressure was removedbefore releasing the remaining gas and opening the autoclave lit.
1: 24% 2: 11%	With oxygen at 130℃; for 2h;	1.2. Typical experiment All the experiments were carried out in a 50 mL stainless steelautoclave supplied by the Anhui Kemi Company equipped with a thermocoupleand magnetic stirrer (800 rpm). Initially, 75 mg of the catalystwas added to 1.5 mmol of the substrate in 15 mL of methanol. Exactly10 bar pressure of O2 was added after purging the reaction thrice. Thereaction mixture was stirred and heated to the desired temperature. Thetarget temperature was achieved after 10-15 min at which point thetime was set to zero. On completion of the reaction, the stirring wasstopped and the autoclave was cooled in the water bath until a temperaturebelow 25C was attained. The residual pressure was removedbefore releasing the remaining gas and opening the autoclave lit.

Reference： [1]He, Liangtu; Huang, Yuzhang; Len, Christophe; Liu, Lei; Miao, Xinge; Wang, Yantao; Yang, Weiran [Molecular catalysis, 2021, vol. 508]
[2]He, Liangtu; Huang, Yuzhang; Len, Christophe; Liu, Lei; Miao, Xinge; Wang, Yantao; Yang, Weiran [Molecular catalysis, 2021, vol. 508]

81
[ 67-56-1 ]
[ 624-45-3 ]
[ 106-65-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	With oxygen at 130℃; for 4h;	1.2. Typical experiment All the experiments were carried out in a 50 mL stainless steelautoclave supplied by the Anhui Kemi Company equipped with a thermocoupleand magnetic stirrer (800 rpm). Initially, 75 mg of the catalystwas added to 1.5 mmol of the substrate in 15 mL of methanol. Exactly10 bar pressure of O2 was added after purging the reaction thrice. Thereaction mixture was stirred and heated to the desired temperature. Thetarget temperature was achieved after 10-15 min at which point thetime was set to zero. On completion of the reaction, the stirring wasstopped and the autoclave was cooled in the water bath until a temperaturebelow 25C was attained. The residual pressure was removedbefore releasing the remaining gas and opening the autoclave lit.

Reference： [1]He, Liangtu; Huang, Yuzhang; Len, Christophe; Liu, Lei; Miao, Xinge; Wang, Yantao; Yang, Weiran [Molecular catalysis, 2021, vol. 508]

82
[ 67-56-1 ]
[ 67-47-0 ]
[ 624-45-3 ]
[ 106-65-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 41% 2: 30%	With oxygen at 130℃; for 2h;	1.2. Typical experiment All the experiments were carried out in a 50 mL stainless steelautoclave supplied by the Anhui Kemi Company equipped with a thermocoupleand magnetic stirrer (800 rpm). Initially, 75 mg of the catalystwas added to 1.5 mmol of the substrate in 15 mL of methanol. Exactly10 bar pressure of O2 was added after purging the reaction thrice. Thereaction mixture was stirred and heated to the desired temperature. Thetarget temperature was achieved after 10-15 min at which point thetime was set to zero. On completion of the reaction, the stirring wasstopped and the autoclave was cooled in the water bath until a temperaturebelow 25C was attained. The residual pressure was removedbefore releasing the remaining gas and opening the autoclave lit.

Reference： [1]He, Liangtu; Huang, Yuzhang; Len, Christophe; Liu, Lei; Miao, Xinge; Wang, Yantao; Yang, Weiran [Molecular catalysis, 2021, vol. 508]

83
[ 98-00-0 ]
[ 67-56-1 ]
[ 624-45-3 ]
[ 106-65-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 27% 2: 46%	With oxygen at 130℃; for 2h;	1.2. Typical experiment All the experiments were carried out in a 50 mL stainless steelautoclave supplied by the Anhui Kemi Company equipped with a thermocoupleand magnetic stirrer (800 rpm). Initially, 75 mg of the catalystwas added to 1.5 mmol of the substrate in 15 mL of methanol. Exactly10 bar pressure of O2 was added after purging the reaction thrice. Thereaction mixture was stirred and heated to the desired temperature. Thetarget temperature was achieved after 10-15 min at which point thetime was set to zero. On completion of the reaction, the stirring wasstopped and the autoclave was cooled in the water bath until a temperaturebelow 25C was attained. The residual pressure was removedbefore releasing the remaining gas and opening the autoclave lit.

Reference： [1]He, Liangtu; Huang, Yuzhang; Len, Christophe; Liu, Lei; Miao, Xinge; Wang, Yantao; Yang, Weiran [Molecular catalysis, 2021, vol. 508]

84
[ 67-56-1 ]
sucrose [ No CAS ]
[ 624-45-3 ]
[ 106-65-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 13% 2: 13%	With oxygen at 130℃; for 2h;	1.2. Typical experiment All the experiments were carried out in a 50 mL stainless steelautoclave supplied by the Anhui Kemi Company equipped with a thermocoupleand magnetic stirrer (800 rpm). Initially, 75 mg of the catalystwas added to 1.5 mmol of the substrate in 15 mL of methanol. Exactly10 bar pressure of O2 was added after purging the reaction thrice. Thereaction mixture was stirred and heated to the desired temperature. Thetarget temperature was achieved after 10-15 min at which point thetime was set to zero. On completion of the reaction, the stirring wasstopped and the autoclave was cooled in the water bath until a temperaturebelow 25C was attained. The residual pressure was removedbefore releasing the remaining gas and opening the autoclave lit.

Reference： [1]He, Liangtu; Huang, Yuzhang; Len, Christophe; Liu, Lei; Miao, Xinge; Wang, Yantao; Yang, Weiran [Molecular catalysis, 2021, vol. 508]

85
[ 106-65-0 ]
[ 34205-71-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; benzaldehyde	P.1.1 (1) (1) Synthesis of methyl 1-hydroxy-3-naphthoate Benzaldehyde (282mmol) and dimethyl succinate (310.2mmol) were put into a round bottom flask, and dissolved in methanol (100mL). When the reactants were well dissolved, 25% Sodium methoxide solution (366.6mmol) was slowly added, and reaction mixture was stirred under reflux for 12 hours. The reaction mixture was acidified with 3M HCl to pH 1, transferred to a separatory funnel, and then extracted three times with dichloromethane. Combined organic layer was dried over MgSO4 and concentrated under reduced pressure to give crude product. The crude product was dissolved in THF (80mL), to which trifluoroacetic anhydride (282mmol) was slowly added, and the reaction mixture was stirred under reflux until the completion of the reaction was observed.

Reference： [1]Current Patent Assignee: LMITO THERAPEUTICS - EP3932909, 2022, A1

86
[ 100-52-7 ]
[ 106-65-0 ]
[ 34205-71-5 ]

Yield	Reaction Conditions	Operation in experiment
30%	Stage #1: benzaldehyde; Dimethyl succinate With sodium methylate In methanol for 12h; Reflux; Stage #2: With trifluoroacetic anhydride In tetrahydrofuran Reflux;	1.1 (1) Synthesis of methyl 1-hydroxy-3-naphthoate benzaldehyde (282mmol) and dimethyl succinate (310.2mmol) were put into a round bottom flask, and dissolved in methanol (100mL). When the reactants were well dissolved, 25% Sodium methoxide solution (366.6mmol) was slowly added, and reaction mixture was stirred under reflux for 12 hours. The reaction mixture was acidified with 3M HCl to pH 1, transferred to a separatory funnel, and then extracted three times with dichloromethane. Combined organic layer was dried over MgSO4 and concentrated under reduced pressure to give crude product. The crude product was dissolved in THF (80mL), to which trifluoroacetic anhydride (282mmol) was slowly added, and the reaction mixture was stirred under reflux until the completion of the reaction was observed. After confirming the completion of the reaction with TLC, the reaction mixture was cooled to room temperature, moved into an ice bath, and then neutralized to pH 7-8 with slow addition of sat. aq. NaHCO3 solution. When neutralization was completed, the reaction mixture was extracted three times with ethyl acetate, and combined organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude product was recrystallized with ethyl acetate and n-hexane, and mother liquor was purified by column chromatography. Yellowish solid, Yield: overall 30%. 1H NMR (300 MHz, CDCl3) δ: 8.26-8.21 (m, 2H), 7.93-7.90 (m, 1H), 7.63-7.51 (m, 3H), 5.95 (s, 1H), 3.98 (s, 3H).

Reference： [1]Current Patent Assignee: LMITO THERAPEUTICS - EP3932909, 2022, A1 Location in patent: Paragraph 0043-0044

87
[ 108-94-1 ]
[ 110-94-1 ]
[ 124-04-9 ]
[ 627-93-0 ]
[ 3878-55-5 ]
[ 110-15-6 ]
[ 13984-57-1 ]
[ 627-91-8 ]
[ 626-86-8 ]
[ 6938-94-9 ]
[ 103-23-1 ]
[ 3128-06-1 ]
bis(1-methylpropyl) 2,2-dimethylpentanedioate [ No CAS ]
[ 123-76-2 ]
[ 539-88-8 ]
[ 123-25-1 ]
[ 106-65-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: cyclohexanone With 7K⁽¹⁺⁾*P₂Mo₅VW₁₂O₆₂^(7-) at 90℃; Stage #2: With dihydrogen peroxide at 90℃; for 20h;	2.2 Catalytic test General procedure: The synthesis method based on the one described inthe literature24 has already been used in our previouswork.22,23 The liquid phase oxidation of cyclohexanone(-one) or the mixture of cyclohexanone (-one)and cyclohexanol (-ol) was carried out at 90 C, usinga 100 mL round-bottom flask equipped with a magneticstirring bar and a reflux condenser. The reactionmixture, consisting of a calculated amount of catalystand substrate, was stirred at 800 rpm; after thereduction of POM, which is manifested by a colourchange from yellow or light green to blue, hydrogenperoxide (30%) was then added dropwise until theinitial colour of POM reappeared. The POM, which isin its oxidized form (yellow or light green colour),continues to oxidize the substrate and after its reduction(blue colour), peroxide is then added dropwiseand so on. The end of the reaction was estimated whenthe catalyst was no longer being reduced. The reactiontime was found to be 20 h. It should be noted that above 90 C, hydrogen peroxide can rapidlydecompose.

Reference： [1]Dermeche, Leila; Idrissou, Yasmina; Mazari, Tassadit; Moudjahed, Mohammed; Rabia, Cherifa [Journal of Chemical Sciences, 2022, vol. 134, # 1]

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P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 106-65-0 ] {[proInfo.proName]}

Quality Control of [ 106-65-0 ]

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Product Details of [ 106-65-0 ]

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Physicochemical Properties

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Lipophilicity

Druglikeness

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Medicinal Chemistry

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Application In Synthesis of [ 106-65-0 ]

[ 106-65-0 ] Synthesis Path-Upstream 1~16

[ 106-65-0 ] Synthesis Path-Downstream 1~87

Related Functional Groups of [ 106-65-0 ]

Aliphatic Chain Hydrocarbons

Esters

Precautionary Statements-General

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Physical hazards

Health hazards

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[ 106-65-0 ]