[ CAS No. 106-33-2 ] {[proInfo.proName]}

Name: 106-33-2|Ethyl Laurate|99%
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Quality Control of [ 106-33-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 106-33-2 ]

Product Details of [ 106-33-2 ]

CAS No. :	106-33-2	MDL No. :	MFCD00015065
Formula :	C₁₄H₂₈O₂	Boiling Point :	-
Linear Structure Formula :	CH₃(CH₂)₁₀COOC₂H₅	InChI Key :	MMXKVMNBHPAILY-UHFFFAOYSA-N
M.W :	228.37	Pubchem ID :	7800
Synonyms :	Ethyl dodecanoate;Lauric Acid ethyl ester;NSC 8912;NSC 83467

Calculated chemistry of [ 106-33-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.93
Num. rotatable bonds :	12
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	70.7
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.64 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.75
Log Po/w (XLOGP3) :	5.71
Log Po/w (WLOGP) :	4.47
Log Po/w (MLOGP) :	3.69
Log Po/w (SILICOS-IT) :	4.52
Consensus Log Po/w :	4.43

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.06
Solubility :	0.0198 mg/ml ; 0.0000869 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.03
Solubility :	0.000214 mg/ml ; 0.000000936 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-4.8
Solubility :	0.00359 mg/ml ; 0.0000157 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	2.35

Safety of [ 106-33-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 106-33-2 ]

* 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 [ 106-33-2 ]
Downstream synthetic route of [ 106-33-2 ]

[ 106-33-2 ] Synthesis Path-Upstream 1~3

1
[ 106-33-2 ]
[ 141-43-5 ]
[ 142-78-9 ]

Reference： [1] Beilstein Journal of Organic Chemistry, 2009, vol. 5,
[2] Journal of Biological Chemistry, 1948, vol. 175, p. 801[3] Journal of the American Chemical Society, 1948, vol. 70, p. 2855
[4] Journal of the American Chemical Society, 1937, vol. 59, p. 111
[5] Patent: US2236530, 1939, ,

2
[ 106-33-2 ]
[ 3262-03-1 ]
[ 19397-74-1 ]

Yield	Reaction Conditions	Operation in experiment
66.3%	With sodium ethanolate In ethanol at 0 - 20℃;	Ethyl decylacetate (0.94 g, 7.8 mmol) was added to a solution of sodium ethoxide (1.1 g, 15.6 mmol) in dry ethanol (8 mL) at 0 ° C. The compound obtained by the method (1.5 g, 7.8 mmol) was added dropwise to the above reaction mixture, and the mixture was stirred at room temperature overnight. After refluxing for half an hour, it was poured into cold brine and extracted with EA (3 X 60 mL). Wash with saturated brine (2×50 mL), dry over anhydrous sodium The crude product is recrystallized from ethanol.1.3 g of a yellow solid was obtained in a yield of 66.3 percent.

Reference： [1] Patent: CN108727416, 2018, A, . Location in patent: Paragraph 0335; 0336; 0337

3
[ 106-33-2 ]
[ 111-42-2 ]
[ 120-40-1 ]

Reference： [1] Journal of the American Chemical Society, 1937, vol. 59, p. 111
[2] Journal of Organic Chemistry, 1955, vol. 20, p. 993

[ 106-33-2 ] Synthesis Path-Downstream 1~46

1
[ 143-07-7 ]
[ 64-17-5 ]
[ 106-33-2 ]

Yield	Reaction Conditions	Operation in experiment
97.2%	With sufonated polystyrene functionalized hollow nanosphere; at 80℃; for 6h;Catalytic behavior;	General procedure: The catalysts were pretreated at 120C under vacuum for 3 hbefore acid-catalyzed reactions.Esterification of lauric acid with ethanol was carried out in atwo-necked round flask equipped with a reflux condenser and amagnetic stirrer. In a typical experiment, 10 mmol of ethanol and2 mmol of lauric acid were added to the flask charged with PS-SO3H/SiO2catalysts (0.04 mmol of H+). The mixture was stirred at80C for 6 h. The products were collected by a syringe at regularintervals and analyzed using a precalibrated gas chromatograph(Agilent 7890) equipped with a flame ion detector (FID) and PEGcapillary column (30 m × 0.25 mm × 0.25 mm). Tetradecane wasused as an internal standard.Transesterification of tripalmitin and methanol was carried outin a two-necked round flask equipped with a reflux condenserand a magnetic stirrer. In a typical experiment, 0.72 mmol of tri-palmitin and 2 mL of methanol were added to the flask chargedwith PS-SO3H/SiO2catalysts (0.04 mmol of H+). The mixture wasstirred at 80C for 21 h. The products were analyzed by Agilent7890 gas chromatography with a flame ionization detector (FID)and HP-INNOWax capillary column (30 m × 0.25 mm × 0.25 mm).Dodecane was used as an internal standard.
95%	With whole cell lipase from a wild-type Aspergillus flavus strain; In hexane; at 40℃; for 24h;	Half a mL of a solution containing 25 mg mL-1 (0.125 mmol mL-1) of lauric acid and ethanol 11.52 mg mL-1 (0.250 mmol mL-1) in hexane was added to a reaction vial (1.5 mL) fitted with a PTFE-lined cap. Then 20 mg of biocatalyst (aw= 0.54) was added to the vial, and the mixture was stirred and heated to 40C for 24 h. The resulting solution was analyzed using GC-FID. Product quantification was achieved using a standard curveobtained from ethyl laurate.
95.3%	With 20percent silica gel supported (N,N-dimethylbenzylammonium)propane sulfonic acid hydrogensulfate immobilized ionic liquid; at 90℃; for 3h;Green chemistry;	To a 100 mL three-necked flask equipped with a constant pressure dropping funnel and a reflux condenser, 10.0 g of lauric acid,18.4g of ethanoland 0.40 g of a 20% catalyst were added, and the reaction was heated in a 90 C oil bath 3.0h. After the end of the reaction, the catalystis separated from the reaction system, and the product is separated by suction filtration. The solid catalyst is washed with ether and dried before being directly used for the next reaction.Evaporation of excess ethanol.Vacuum distillation of ethyl laurate, gas chromatography for purity detection.

91.3%	With 8-hydroxyquinoline sulphate; at 85℃; for 4h;	In a 100 mL three-necked flask, 0.05 mol of lauric acid, 0.30 mol of ethanol and 0.025 mol were added8-hydroxyquinoline bisulfate ionic liquid, the temperature of the reaction system is controlled at about 85 , equipped with reflux condenser, stirring at constant temperature for 4h. After the reaction was stopped, unreacted residual ethanol was removed, the mixture was transferred to a separatory funnel, washed with an appropriate amount of saturated brine,Shake, to be layered, discard the lower water, keep the upper oil, repeated washing 2 to 3 times, the final oil is the product of ethyl laurate, the yield of 91.3%.
86.3%	With SO3H-phenylenesilica hollow nanospheres; at 80℃; for 6h;Catalytic behavior;	Typically, the desired amount of solid acids (0.05 mmol H+) was added into a two-necked round flask equipped with a reflux condenser and a magnetic stirrer. Then 10 mmol of ethanol and 2 mmol of lauric acid were added to the flask and the mixture was stirred at 80 C for 6 h. The activity in esterification was evaluated by yield of ethyl laurate. Reaction products were analyzed using a gas chromatograph (GC Agilent-6890A) equipped with an FID as well as a PEG capillary column using tetradecane as internal standard.
81%	With hydroxy-substituted sulfonic acid-functionalized silica (HO-SAS); at 110℃;Flow reactor;	General procedure: Lauric acid (1a) (2.01 g, 10.0 mmol) was dissolved in methanol (10 mL) and then placed in a syringe, which wasthen attached to a syringe pump. The methanol solution was fedinto a stainless steel column (inner volume: 0.53 mL, 4.0 mm i.d. 50 mm) filled in HO-SAS (334 mg) with a flow rate of0.177 mL.min-1. The column was immersed into an oil bath(110C). A back-pressure regulator (75 psi) was connected.The reaction mixture was collected from the outlet. The reaction mixture eluted during the first 10 min was discarded. Thereaction mixture was collected during 3 min and added n-decane as an internal standard for GC analysis. The followingportion was collected for a 30 min period in a glass flask, andsolvent was evaporated. The crude mixture was purified byflash column chromatography on SiO2 (hexane/ethyl acetate =5/1) to give 3a (1.13 g, 99%).
74%	With glycine ethyl ester hydrochloride; In cyclohexane; at 78℃; for 6h;	Into a 500 mL three-necked flask equipped with a thermometer and a water separator, add 150 mL of absolute ethanol, 40 g (0.2 mol) of lauric acid,After stirring and mixing uniformly, 50 mL of cyclohexane and 2.52 g (0.02 mol) of glycine methyl ester hydrochloride were added, and the temperature was raised to reflux (temperature: 78 C.) to react for 6 hours.After cooling down to room temperature, the solvent was recovered by concentration, and 50 mL of water was added to the concentrate.Then 150 mL of ethyl acetate was added and extracted once.The ethyl acetate layer was washed twice with 50% aqueous 5% sodium chloride, each 50 mL.The ethyl acetate layer was concentrated to obtain 48.4 g of a crude product, which was distilled under reduced pressure.Collect 174-179oC / 0.06MPa products,33.8 g of ethyl laurate was obtained as the final product. The final product was a pale yellow oily liquid.The purity by gas chromatography was 97.2% and the reaction yield was 74%. The structure was confirmed by nuclear magnetic characterization.
80%Chromat.	With sulfuric acid; for 4h;Reflux;	General procedure: General procedure for the synthesis of compounds (6a-p); organic acid (0.40 mmol.), and catalyst (0.0005 mmol.) was combined with 20 mL ethanol in a 50 mL round bottomed flask equipped with a stir bar. Reaction was allowed to stir at reflux temperature for the appropriate amount of time (4 h). After completion of reaction, the reaction mixture was concentrated in vacuum to give a crude product which was analyzed by 1H NMR and GC-MS.
81%Chromat.	With trimethylcyclohexylammonium methanesulfonate; toluene-4-sulfonic acid; at 60℃; for 2h;	General procedure: Equimolar amounts of quaternary ammonium salt (1.5 mmol) and p-toluenesulfonic acid monohydrate (Sigma-Aldrich, 98,5+% used as received) were mixed in a screw-capped 3 ml vial. The mixture was magnetically stirred and heated to 60 C until a clear colourless liquid was obtained (about 10 min). DES was used right after its preparation. Equimolar amounts (4.5 mmol) of acid and alcohol were added, and the resulting mixture, was heated to 60 C (or 80 C if specified) and magnetically stirred for the specified amount of time. Initially the reaction mixture is homogeneous and fluid, and then a heterogeneous system formed as reaction proceeded, due to insolubility of the esters produced in the DES. For the g.c. analysis further elaboration was as follows. At the end of the reaction, tbutylbenzene was added, as the internal standard, to the mixture, which was then extracted with diethyl ether. Organic layer was washed with NaHCO3, dried over Na2SO4 and analyzed by g.c.
	With Hp-E mesoporous zeolite;	The catalytic reactions were carried out in a three-necked round bottom flask equipped with a reflux condenser (351 ± 2 K), a thermometer and a sampling system. The whole system was kept in an oil bath, which was placed upon a magnetic stirrer. A certain amount of lauric acid and ethanol to form totally 5 ml mixture with the molar ratio between lauric acid and ethanol fixed at 1:4. Then, 0.1 g catalyst was added into the mixture. The yield of ethyl laurate was determined periodically by using GC-MS (Agilent, 6890/5973 N).
	With sulfuric acid; for 10h;Reflux;	A mixture of lauric acid (1) (2 g, 0.01 mol), absolute ethanol (50 mL) and conc. H2SO4 (0.5 ml) was refluxed for 8-10 h in a round bottom flask and then cooled to 5 C.The solvent was removed by distillation and the reaction mixture washed with 1 % aqueous sodium bicarbonate solution. The reaction mixture was extracted with ethyl acetate and the solid separated was dried over magnesium sulfate, filtered, and collected to obtain compound 2.
	With SO3H-phenylenesilica hollow nanospheres; at 80℃; for 6h;Catalytic behavior;	Typically, the desired amount of solid acids (0.05 mmol H+) was added into a two-necked round flask equipped with a reflux condenser and a magnetic stirrer. Then 10 mmol of ethanol and 2 mmol of lauric acid were added to the flask and the mixture was stirred at 80 C for 6 h. The activity in esterification was evaluated by yield of ethyl laurate. Reaction products were analyzed using a gas chromatograph (GC Agilent-6890A) equipped with an FID as well as a PEG capillary column using tetradecane as internal standard.
	With zirconium containing 2-aminoterephthalate metal organic framework; at 78℃; for 8h;Catalytic behavior;	General procedure: Esterification reactions were performed as follows: 1 mmol offatty acid, and the desired amount of alcohol were contacted withthe MOF (0.07 mmol Zr) in a batch reactor at the specified tem-perature (see footnotes in the corresponding tables for specificconditions). The reaction was followed by GC-MS (Varian 3900)with a 30 m long and 0.25 mm i.d. capillary column HP-5 (5%phenylmethylpolysiloxane), using dodecane as external standard.Retention times were compared with those of commercial stan-dards. Turnover frequencies (TOFs) of the Zr-MOFs were calculatedas moles of product formed per moles of zirconium present inthe reaction (considering that all the zirconium atoms of the MOFare participating in the reaction) and per hour. Data were takenat short reaction times corresponding to low levels of conversion(<15-20%).
	With thionyl chloride; for 2h;Reflux;	General procedure: To a stirred solution of carboxylic acid (1.0 eq.) in ethanol (2 M) was added thionyl chloride (2.0 eq.) dropwise at room temperature, and then refluxed for 2 hours. After it was cooled to room temperature, the reaction mixture was concentrated under reduced pressure to give crude product, which was chromatographed on silica gel column using 1:30 (v/v) EtOAc-petroleum ether solution as eluent to afford isolated product esters in 80% - 95% yields. Esters (1.0 eq.) were added dropwise to a stirred solution of acetonitrile (2.0 eq.) and NaH (3.0 eq.) in THF (2 M) at room temperature, and then refluxed for 1h . After it was cooled to room temperature, Water was added dropwise to the reaction mixture under ice bath until no gas bubbles generated, and employing dilute hydrochloric acid neutralization to neutral, extracted with ethyl acetate, dried over magnesium sulfate and concentrated in vacuo to give crude product which was chromatographed on silica gel column using 1:4 to 1:2 (v/v) EtOAc-petroleum ether solution as eluent to afford isolated product beta-ketonitriles, white or light yellow solid compounds in 50% - 85% yields. Finally, stirred in concentrated sulfuric acid (3 M) at room temperature for 5 to 10 hours. The reaction mixture was neutralized to neutral by ammonia water, extracted with ethyl acetate, dried over magnesium sulfate and concentrated in vacuo to give crude product which was chromatographed on silica gel column using 1:1 to 2:1 (v/v) EtOAc-petroleum ether solution as eluent to afford isolated product beta-ketoamides 1a-p, white solid compounds in 45% - 85% yields.
	With trimethylcyclohexylammonium methanesulfonate; toluene-4-sulfonic acid; at 60℃; under 760.051 Torr; for 3h;	According to the flow of Figure 2, the following processing is performed:2.5 mol of dodecanoic acid, 3.125 mol of ethanol and 3.75 mol of trimethylcyclohexylammonium methanesulfonate-p-toluenesulfonic acida eutectic solvent (the molar ratio of trimethylcyclohexylammonium methanesulfonate to p-toluenesulfonic acid is 1:2) is added to the esterification reactor,The esterification reactor was heated to 60 C, and the reaction was stirred at normal pressure for 3 hours, and the stirring speed was 1000 rpm. Introducing the reaction solution after the reactionThe decanter was allowed to stand for phase separation and the rest time was 3 h. The upper liquid (ester phase) and the lower liquid obtained after phase separation in the decanter(Water phase) is introduced into the washing tank and the flash tank respectively to carry out product ester purification and raw materials (mainly eutectic solvents, carboxylic acids and alcohols)Recycling. The working pressure of the washing tank is normal pressure, the operating temperature is room temperature, and the mass fraction is taken from the top of the washing tank.91% product, ethyl dodecanoate, a high-purity ester, a mixture of eutectic solvent and water at the bottom, introduced into a flash tank; flashingThe tank has an operating pressure of 0.001 bar and an operating temperature of 125 C. The unreacted raw material is taken from the top of the flash tank and containsA mixture of water and ester with a eutectic solvent having a mass fraction of 99.99% at the bottom. Low eutectic solution obtained at the bottom of the flash tankThe agent is respectively exchanged to a temperature of 60 C through a heat exchanger and returned to the esterification reactor for recycling. Mixture produced at the top of the flash tankThe alcohol recovery tower is introduced, the actual number of trays of the alcohol recovery tower is 40, the operating pressure is normal pressure, and the operation reflux ratio is 5.7. The alcohol recovery towerThe unreacted alcohol was obtained from the top of the column, and was cooled to 60 C by a heat exchanger, and then returned to the esterification reactor for recycling. Recycling alcoholThe material of the Tata kettle is introduced into the carboxylic acid recovery column. The actual number of plates in the carboxylic acid recovery column is 45, the operating pressure is normal pressure, and the operation is refluxed.The ratio is 3.8, the by-product water is obtained at the top of the acid recovery tower, and finally the water is removed from the esterification reaction system, and the acid recovery tower is obtained.The column kettle is obtained as a mixture containing unreacted carboxylic acid and a part of the product, and is cooled to 60 C by a heat exchanger to return to the esterification reaction.The kettle should be recycled. The yield of ethyl dodecanoate in Example 16 was 99.3%, and the purity was 91%.
	With sulfuric acid; at 20℃; for 12h;	General procedure: Prior to Gas Chromatography-Mass Spectrometry (GC-MS) analysis, active fractions andcommercial decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, and tetradecanoic acid(purity > 98%; Sigma-Aldrich, St. Louis, MI, USA) were methylated and ethylated. Samples (30 mg)were diluted with 10 mL acidified methanol or ethanol (1% sulfuric acid) and stirred for 12 h at roomtemperature. The product of the reaction was suspended in an aqueous solution of 20% Na2CO3(20 mL) and extracted with CHCl3 (3, 20 mL, each one) and the solvent was eliminated under vacuumuntil dry. These derivatives were stored at 4 C until use in assays [60].

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2
[ 106-33-2 ]
[ 1120-21-4 ]

Reference： [1]The journal of the Society of Chemical Industry, Japan. Supplemental binding.,vol. 42,p. 18
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3
[ 106-33-2 ]
[ 112-54-9 ]

Yield	Reaction Conditions	Operation in experiment
99%		The following experimental procedure for the partial reduction of ethyl dodecanoate to benzaldehyde is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with morpholine (0.18mL, 2.1mmol) and 10mL THF. After cooling to 0C, DIBALH (2.0mL, 1.0M in hexane, 2.0mmol) was added dropwise and stirred for 3h at same temperature. To a reaction mixture was slowly added ethyl dodecanoate (0.23g, 1.0mmol) and stirred for 10min. Then, LDBMA (2.8mL, 0.46M in hexane-THF, 1.3mmol) was added and the mixture was stirred for 10min again. The reaction was stopped by the aqueous 1N HCl (10mL) and extracted with diethyl ether (2×10mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of the residue by short column chromatography on silica gel using Et2O yielded dodecanal (183mg, 99%).

Reference： [1]Tetrahedron,2014,vol. 70,p. 4420 - 4424
[2]Patent: US2105540,1935,

4
[ 106-33-2 ]
[ 1120-16-7 ]

Reference： [1]Diss.<Freiburg i.Br.1886>,S.13,

5
[ 106-33-2 ]
[ 112-53-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen; In tetrahydrofuran; at 100℃; under 38002.6 - 76005.1 Torr; for 15h;Glovebox; Autoclave;	General procedure: In a glove box, add a ruthenium complex Ia (0.3 to 0.7 mg, 0.0002 to 0.001 mmol) to a 300 mL autoclave,Potassium methoxide (35-700 mg, 0.5-10 mmol), tetrahydrofuran (4-60 mL), and ester compounds (10-200 mmol).After sealing the autoclave, take it out of the glove box and fill it with 50 100atm of hydrogen.The reaction kettle was heated and stirred in an oil bath at 100 C for 10 to 336 hours.After the reaction kettle was cooled in an ice-water bath for 1.5 hours, the excess hydrogen was slowly released.The solvent was removed from the reaction solution under reduced pressure, and the residue was purified with a short silica gel column to obtain an alcohol compound. The results are shown in Table 5.

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[10]Patent: DE164294,

6
[ 106-33-2 ]
[ 5399-22-4 ]

Yield	Reaction Conditions	Operation in experiment
1.93 g	With hydrazine hydrate; In ethanol; for 6h;Reflux;	To a solution of 2 (2.28 g, 0.01 mmol) in absolute absolute ethanol (30 mL), hydrazine hydrate (0.64 g, 0.02 mol) was added and the reaction mixture was heated under reflux for 6 h and then left to cool. The solid product was collected by filtration and purified by crystallization form ethanol. White powder, (1.93 g, 85 %), mp. 115-117 C. IR (m/cm-1): 3342-3225 (NH, NH2), 2953, 2848 (CH in alkyl chain) and 1676 (C=O). 1HNMR: delta 6.83 (s, 1H, NH), 3.92 (s, 2H,NH2),0.95 (t, 3H, terminal CH3), 1.40-1.25 (m, 20H, CH2 in alkylchain). Anal. Calc. for C12H26N2O (214.35): C, 67.24; H,12.23; N, 13.07 %. Found: C, 66.98; H, 11.97; N, 12.78 %.

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[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2010,vol. 49,p. 526 - 531
[5]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 838 - 845
[6]Chinese Chemical Letters,2011,vol. 22,p. 1293 - 1296
[7]Journal of Surfactants and Detergents,2015,vol. 18,p. 661 - 673

7
[ 106-33-2 ]
[ 96179-66-7 ]

Reference： [1]Journal of the American Chemical Society,1933,vol. 55,p. 1698
[2]Journal of the Chemical Society. Chemical communications,1990,p. 711 - 712

8
[ 106-33-2 ]
[ 141-43-5 ]
[ 142-78-9 ]

Reference： [1]Beilstein Journal of Organic Chemistry,2009,vol. 5
[2]Journal of Biological Chemistry,1948,vol. 175,p. 801
Journal of the American Chemical Society,1948,vol. 70,p. 2855
[3]Journal of the American Chemical Society,1937,vol. 59,p. 111

9
[ 106-33-2 ]
[ 111-42-2 ]
[ 120-40-1 ]

Reference： [1]Journal of the American Chemical Society,1937,vol. 59,p. 111

10
[ 106-33-2 ]
[ 143-07-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With 2C33H37N*H2O7S2; water; at 60℃; for 20h;	General procedure: [Example 2] Production of Lauric Acid (and Methanol) by Hydrolysis of Methyl Laurate[0059] After m<strong>[106-33-2]ethyl laurate</strong> (2 mmol) and water (1 to 8 mL) were added to the ammonium pyrosulfate catalyst (5 mol%)obtained in Example 1(1), heating was performed at 60C for 24 hours while stirring was performed, so that a hydrolysisreaction of m<strong>[106-33-2]ethyl laurate</strong> was performed. The reaction mixture thus obtained was partly sampled and was analyzed by1H NMR (CDCl3), so that the yield of lauric acid was calculated. The chemical shifts (ppm) are shown below. In addition,the results are shown in Table 1.M<strong>[106-33-2]ethyl laurate</strong>: delta 0.88 (t, J=6.6 Hz, 3H), 1.29 (m, 16H), 1.62-1.65 (m, 2H), 2.30 (t, J=7.5 Hz, 2H), 3.66 (s, 3H)Lauric acid: delta 0.89 (t, 3H), 1.16-1.37 (m, 16H), 1.64 (q, J=7.3, 2H), 2.35 (t, J=7.3 Hz, 2H)

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 1029 - 1033
[2]Patent: EP2799422,2014,A1 .Location in patent: Paragraph 0063; 0064; 0065
[3]Journal of Organic Chemistry,1981,vol. 46,p. 1991 - 1993
[4]Organic Letters,2012,vol. 14,p. 3194 - 3197

11
[ 106-33-2 ]
[ 111-27-3 ]
[ 64-17-5 ]
[ 34316-64-8 ]

Yield	Reaction Conditions	Operation in experiment
	With Lipase enzyme preparation In benzene Ambient temperature; Lipases catalyzed transesterification;

Reference： [1]Therisod, Michel [Journal of Organometallic Chemistry, 1989, vol. 361, p. C8 - C10]

12
[ 2017-01-8 ]
[ 1120-16-7 ]
[ 106-33-2 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 1759 - 1761

13
[ 106-33-2 ]
[ 23323-37-7 ]
Dodecanoic acid (2R,3R,4R,5S)-2,3,4,5-tetrahydroxy-6-octylamino-hexyl ester [ No CAS ]
n-dodecanoyl-N-octyl-glucamide [ No CAS ]
Dodecanoic acid (2R,3R,4R,5S)-6-(dodecanoyl-octyl-amino)-2,3,4,5-tetrahydroxy-hexyl ester [ No CAS ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 5185 - 5194

14
[ 106-33-2 ]
[ 62774-20-3 ]
[ 34316-64-8 ]

Yield	Reaction Conditions	Operation in experiment
	With Lipase enzyme preparation In benzene Ambient temperature; Lipases catalyzed transesterification;

Reference： [1]Therisod, Michel [Journal of Organometallic Chemistry, 1989, vol. 361, p. C8 - C10]

15
[ 106-33-2 ]
[ 112-53-8 ]
[ 7289-37-4 ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 4985 - 4988

16
[ 64-17-5 ]
[ 538-24-9 ]
[ 106-33-2 ]

Yield	Reaction Conditions	Operation in experiment
Ca. 90%	With SBA-15-SO3H; at 230℃; for 1.5h;Kinetics;	The experimental device has been described in detail in our previous work [16]. Transesterification reactions were performed with triacylglycerol and liquid ethanol with a mass ratio of 1:10. The SBA-15-SO3H catalyst with 5.0 wt% loading was placed in the 4-mL reactor,which was vertically positioned in a Techne fluidized sand bath (model SBL-2). In addition, different kinds of catalysts were used, and then, thebest was selected as the core catalyst in this study. The transesterification reaction was carried out at a series of temperatures, i.e., 160,180, 200 and 230 C, with a series of times of 15, 30, 45, 60, 75 or 90 min. The vessels were removed from the sand bath and cooled to room temperature. At last, the products were washed with methanol at least three times so that all products were recovered. The products were analysed by HPLC equipped with an AcclaimTMC18 column (4.6mm i.d.×250mm length). HPLC was conducted using a mobile phase of 65% methanol and 35% acetonitrile at a flow rate of 0.8 mL/min for 25 min. The UV detector was set at 210 nm, andthe column temperature was 35.0 C

Reference： [1]Inorganica Chimica Acta,2018,vol. 482,p. 846 - 853
[2]Journal of Organometallic Chemistry,2006,vol. 691,p. 1965 - 1972

17
[ 44855-57-4 ]
[ 106-33-2 ]
(R)-N-(octan-2-yl)dodecanamide [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 837 - 839

18
[ 1120-16-7 ]
[ 106-33-2 ]

Reference： [1]Synthetic Communications,1997,vol. 27,p. 923 - 937

19
[ 27563-67-3 ]
[ 106-33-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Na₂HPO₄ / CH₂Cl₂ / 12 h / 0 - 20 °C 2: 107.3 mg / HCl / H₂O / Ambient temperature; 4-5 h

Reference： [1]Kiessling, Anthony J.; McClure, Cynthia K. [Synthetic Communications, 1997, vol. 27, # 5, p. 923 - 937]

20
[ 106-33-2 ]
[ 10443-61-5 ]

Reference： [1]Journal of the American Chemical Society,1935,vol. 57,p. 2424

21
[ 106-33-2 ]
[ 62774-20-3 ]
[ 34316-64-8 ]
[ 682-00-8 ]

Yield	Reaction Conditions	Operation in experiment
	With lipase catalyst In benzene refluxing (8 h, azeotropic removal of water); not isolated, IR spectroscopy;

Reference： [1]Therisod, Michel [Journal of Organometallic Chemistry, 1989, vol. 361, p. C8 - C10]

22
[ 65500-28-9 ]
[ 106-33-2 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 1005 - 1008

23
[ 2969-81-5 ]
[ 1192466-35-5 ]
[ 106-33-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium phosphate monohydrate;palladium diacetate; tricyclohexylphosphine; In tetrahydrofuran; at 20℃; for 22h;Inert atmosphere;	Example 7:; Suzuki coupling of ethyl-4-bromobutanoate and B-octyl-9-BBN-2-picoline complex (sp3- sp3); <n="13"/> 1.38 g (6 mmol) of solid potassium phosphate (K3PO4.H2O), 50 mg (0.2 mmol) of PaI- ladium-(ll)-acetate (Pd(OAc)2) and 1 12 mg (0.4 mmol) of tricyclohexylphophine (P(Cy)3) were mixed. The mixture was purged with nitrogen for 15 minutes and then 5.88 ml of a 1.02 M solution of B-octyl-9-BBN-2-picoline complex (6 mmol) in THF was added to the solids. The mixture was diluted with 5.9 ml anhydrous THF and treated with ethyl-4-brombutanoate (975 mg, 5.0 mmol). The black suspension was stirred for 22 h at room temperature, than hydrogen peroxide (H2O2, 30w%, 2 ml) was added and stirring was continued for another 10 minutes. After that, diethyl ether (20 ml), followed by water (5 ml) was added. The aqueous layer was separated from the organic layer and extracted twice with diethyl ether (2 x 15 ml). The combined organic layers were dried over sodium sulfate (Na2SU4), filtered and evaporated to dryness. The crude product was purified by column chromatography on silica gel (pure hexane) to result in 870 mg (73 %) of ethyl dodecanoate as a colorless oil.

Reference： [1]Patent: WO2009/133045,2009,A1 .Location in patent: Page/Page column 11-12

24
[ 106-33-2 ]
[ 57-50-1 ]
[ 20881-05-4 ]
[ 13039-40-2 ]
sucrose-6,6'-di-O-laurate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In dimethyl sulfoxide at 70℃; Ultrasonic irradiation;

Reference： [1]Location in patent: experimental part Huang, Dan; Jiang, Xue; Zhu, Hao; Fu, Xiaorong; Zhong, Kangrong; Gao, Weidong [Ultrasonics Sonochemistry, 2010, vol. 17, # 2, p. 352 - 355]

25
[ 106-33-2 ]
[ 2437-25-4 ]

Yield	Reaction Conditions	Operation in experiment
79%		General procedure: NaOtBu (98% purity, 206 mg, 2.1 mmol) was dried by a vacuum pump for 30 min at room temperature. To a solution of NaOtBu in THF (3 mL) was added DIBAL-H (1.04 M, 1.92 mL, 2.0 mmol) at 0 C under argon atmosphere and the obtained mixture was stirred for 1 h at room temperature. Then, ethyl decanoate (200.32 mg, 1.0 mmol) in THF (4 mL) was added to the solution at 0 C, and the obtained mixture was stirred for 2 h. Then, DIH (1.13 g, 3.0 equiv) and aq NH3 (concentration: 28.0%-30.0%, 2 mL), were added at 0 C, and the obtained mixture was stirred for 3 h at room temperature. Then, the reaction mixture was poured into saturated aq Na2SO3 solution (10 mL) and extracted with ethyl acetate (15 mL×3). The organic layer was dried over Na2SO4. After removal of the solvent under reduced pressure, the residue was treated with flash short column chromatography on Silica gel (eluent: hexane/ethyl acetate=9:1) to afford decanenitrile (119.5 mg, 79% yield).

Reference： [1]Tetrahedron,2011,vol. 67,p. 7956 - 7962

26
[ 67-56-1 ]
[ 106-33-2 ]
[ 111-82-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With Merrifield resin-supported N3=P(MeNCH2CH2)3N; at 23 - 25℃; for 6h;Inert atmosphere;	General procedure: A round bottom centrifuge tube containing catalyst 4 (6.7 mol % based on the percent phosphorus determined by elemental analysis or as otherwise stated in the footnotes of the corresponding Tables) was equipped with a rubber septum and two magnetic stir bars for extra stirring efficiency. After flushing the tube with argon, it was charged via syringe with a higher ester (5 mmol) and MeOH (5 mL) for transesterifications. For amidations, the tube was similarly charged with an ester (2 mmol), amino alcohol (2 mmol), and THF (3 mL). The reaction mixture was vigorously stirred at room temperature (23-25 C) and progress of the reaction was monitored by thin layer chromatography. Upon completion of the reaction, the reaction mixture was filtered through Whatman No. 1 filter paper and washed with 3 × 10 mL of THF. The combined organics were subjected to short-path silica gel chromatography (0-20% ethyl acetate in hexanes v/v) to obtain an analytically pure product. In the case of amides, products were purified using a short-path silica gel column eluted with dichloromethane/methanol (95:5, v/v).

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 6523 - 6529

27
Dess-Martin periodinane [ No CAS ]
NaHCO₃ (sat. aq.) [ No CAS ]
[ 106-33-2 ]
Benzyl ((S)-3-(4-((tert-butyloxycarbonylamino) methyl) phenyl)-1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-yl) carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tert.-butylhydroperoxide; sodium thiosulfate;vanadyl acetylacetonate; In decane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; ethyl acetate;	Benzyl ((S)-3-(4-((tert-butyloxycarbonylamino) methyl) phenyl)-1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-yl) carbamate (14) Allylic alcohol 13 (1.79 g, 3.94 mmol) was dissolved in DCM (25 mL) and cooled to 0 C. after which vanadyl acetylacetonate (0.1 eq., 0.4 mmol, 107 mg) and tBuOOH (3 eq., 12.0 mmol, 2.18 mL; 5.5 M in decane) were added and the mixture was stirred at 0 C. until TLC analysis indicated complete consumption of starting material after 2 hours. The mixture was concentrated under reduced pressure, redissolved in EtOAc and extracted with half sat. aq. NaHCO3, H2O and brine, dried over MgSO4 and concentrated under reduced pressure. The resulting product was quickly purified by column chromatography (20%?60% EtOAc/PE) and immediately subjected to the next step because of the possible instability of the intermediate. The compound was dissolved in DCM (25 mL) and Dess-Martin periodinane (3 eq., 11.0 mmol, 4.50 g) was added. The mixture was stirred at room temperature for 12 hours after which TLC analysis indicated complete conversion. Next, a 1:4 (v/v) mixture (150 mL) of NaHCO3 (sat. aq.)/Na2S2O3 (1 M aq.) and the resulting emulsion was stirred vigorously for 30 minutes after which the layers were separated and the aqueous layer extracted with DCM. The combined organic layers were extracted with sat. aq. NaHCOD dried over MgSO4 and concentrated under reduced pressure. The title compound was obtained after column chromatography (20%?30% EtOAc/PE) as a colourless oil (yield: 1.03 g, 2.20 mmol, 56%). 1H NMR (400 MHz, CDCl3): delta=7.33-7.22 (m, 5H), 7.16 (d, J=7.94 Hz, 2H), 7.08 (d, J=7.95 Hz, 2H), 5.51 (d, J=8.19 Hz, 1H), 5.06-5.01 (m, 1H), 4.97 (d, J=4.39 Hz, 2H), 4.60 (dd, J=12.65, 7.86 Hz, 1H), 4.24 (d, J=4.36 Hz, 2H), 3.26 (d, J=4.62 Hz, 1H), 3.08 (dd, J=13.96, 4.48 Hz, 1H), 2.87 (d, J=4.53 Hz, 1H), 2.70 (dd, J=13.88, 8.12 Hz, 1H), 1.49 (s, 3H), 1.44 (s, 9H) ppm. 13C NMR (100 MHz, CDCl3):delta=207.77, 155.74, 155.66, 137.61, 135.97, 134.62, 129.32, 128.26, 127.91, 127.76, 127.44, 79.15, 66.62, 58.99, 54.07, 52.12, 44.07, 36.61, 28.21, 16.34 ppm. [alpha]D23=+82.2 (c=1, CHCl3).

Reference： [1]Patent: US2012/214732,2012,A1

28
[ 64-17-5 ]
[ 1956-11-2 ]
[ 106-33-2 ]

Yield	Reaction Conditions	Operation in experiment
	With induced mycelium-bound lipase from Aspergillus niger MYA 135 In hexane; acetone at 37℃; for 1h; Enzymatic reaction;

Reference： [1]Romero, Cintia M.; Pera, Licia M.; Loto, Flavia; Baigori, Mario D. [Catalysis Letters, 2012, vol. 142, # 11, p. 1361 - 1368]

29
[ 1427085-08-2 ]
[ 111-82-0 ]
[ 106-33-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example 11 Method for Producing Methyl Dodecanoate and Ethyl Dodecanoate from Ethyl 6-(5-acetylfuran-2-yl)-4-oxohexanoate [0070] Furfural, ethyl levulinate, and acetic anhydride are reacted to form the starting compound ethyl 6-(5-acetylfuran-2-yl)-4-oxohexanoate, according to a method described in the Gordon applications, the entire disclosure of which are incorporated herein by reference. [0071] For the hydrogenation reaction, 300 g of ethyl 6-(5-acetylfuran-2-yl)-4-oxohexanoate and 3.0 g of 64 weight percent Ni on Silica catalyst are added to a 600 mL stirred Parr reactor. Alternative catalysts such as Rh, Re, Ru, Pd, Pt, Ir, Cu, Cr, or Fe on supports such as carbon, silica, or alumina can also be used. The reactive conditions will be selected to produce a reduced mixture for example where the furan ring is substantially hydrogenated. The reactor is purged of air using vacuum and nitrogen cycles and then is charged with hydrogen gas to an initial pressure of 200 psig. The system is run at 200 psig of hydrogen gas with temperatures of 75 C. for 4 hours, then 100 C. for 2 hours, and then 125 C. for 100 hours. The resulting reduced mixture includes but is not limited to ethyl 6-(5-acetyltetrahydrofuran-2-yl)-4-oxohexanoate, ethyl 6-(5-acetyltetrahydrofuran-2-yl)-4-hydroxyhexanoate, or 5-(2-(5-acetyltetrahydrofuran-2-yl)ethyl)dihydrofuran-2(3H)-one. [0072] For the hydrodeoxygenation reaction, an appropriate catalyst such as Ni on SiAl, Pt on SiAl, or other precious metals such as Rh, Re, Ru, Pd, Pt, Ir, Cu, Cr, or Fe on an acidic support, is prepared and activated as described in previous Examples. The hydrogenation products are dissolved at 50 weight percent in methanol. The solution is pumped at 0.03 mL/min over 1 g of catalyst (LHSV?0.6 hr-1) packed in a one-quarter inch stainless steel tube at a temperature range of 220 C. to 240 C., pressure of 470 psig of hydrogen and hydrogen gas feed of 100 mL/min(GHSV?2000 hr-1). The effluent is collected, and methyl decanoate and ethyl dodecanoate are isolated from the spontaneously separating organic phase.

Reference： [1]Patent: US2013/66089,2013,A1 .Location in patent: Paragraph 0070; 0071; 0072

30
[ 1427085-03-7 ]
[ 143-07-7 ]
[ 106-33-2 ]
ethyl 7-(5-methyltetrahydrofuran-2-yl)heptanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28.7%; 58.2%; 13%	With hydrogen; In neat (no solvent); at 240℃; under 25066.7 Torr; for 28h;	Neat ethyl 7-(5-methyltetrahydrofuran-2-yl)-5-oxoheptanoate was flowed at a pressure of 470 psig, and temperature of 240 C. under flowing hydrogen gas for 28 hours. The liquid flow rate and hydrogen gas flow rates were kept constant relative to each other, e.g. 0.03 mL/min liquid flow and 30 mL/min gas flow; 0.06 and 60 mL/min; or 0.09 and 90 mL/min The effluent was primarily organic with a small spontaneously separating water layer beneath the organic phase. Not counting the startup and shutdown, 62.9 g of organic phase was collected out of a theoretical 68.5 g, or 91.9%. GCMS analysis revealed an initial high concentration of 58.2% ethyl dodecanoate, 28.7% dodecanoic acid, and 13% intermediates, possibly ethyl 7-(5-methyltetrahydrofuran-2-yl)heptanoate.

Reference： [1]Patent: US2013/66089,2013,A1 .Location in patent: Paragraph 0060

31
[ 1427085-03-7 ]
[ 1454314-43-2 ]
[ 143-07-7 ]
[ 106-33-2 ]

Yield	Reaction Conditions	Operation in experiment
6%; 93%	With hydrogen; In ethanol; water; at 240℃; under 25066.7 Torr; for 144h;	The production of the starting compound, 7-(5-Methyl-furan-2-yl)-5-oxo-hept-6-enoic acid ethyl ester, and hydrogenation reaction were performed as described in Example 6. For the hydrodeoxygenation reaction, ethyl 7-(5-methyltetrahydrofuran-2-yl)-5-oxoheptanoate and ethyl 5-hydroxy-7-(5-methyltetrahydrofuran-2-yl)heptanoate were dissolved at 15 weight percent to 17 weight percent in a water and ethanol solution composed of about 60% water and about 40% ethanol. The solution was pumped at a rate of 0.08 mL/min (LHSV?0.3 hr-1) over the 7.08 g Pt on SiAl tubular bed described in Example 3 at a temperature of 240 C., pressure of 470 psig and hydrogen gas feed of 30 mL/min (GHSV?100 hr-1) for 6 continuous days. The effluent from the flow reactor spontaneously separated into two components: a less dense organic phase, and a more dense aqueous phase. The organic phase was collected and analyzed. A total of 78.5 g of organic phase was collected, including start up and shut down. GCMS analysis showed the major components to be 93% ethyl dodecanoate and 6% dodecanoic acid.

Reference： [1]Patent: US2013/66089,2013,A1 .Location in patent: Paragraph 0062

32
[ 30089-00-0 ]
[ 2969-81-5 ]
[ 106-33-2 ]

Yield	Reaction Conditions	Operation in experiment
66 mg	With [((Me)NN2)NiCl]; isopropyl alcohol; sodium iodide; sodium hydroxide; In 1,4-dioxane; isopropyl alcohol; at 80℃; for 24h;Inert atmosphere;	General procedure: To a solution of NaOH (32 mg, 0.8 mmol, 1.6 equiv), catalyst 1 (8.4mg, 0.025 mmol, 5 mol%), NaI (37 mg, 0.25 mmol, 0.5 equiv), and i-PrOH (76 muL, 1 mmol, 2 equiv) in dry 1,4-dioxane (2.4 mL), were added alkyl halide (0.5 mmol) and the alkyl-(9-BBN) (1.6 mL, 0.8mmol, 1.6 equiv) under a N2 atmosphere. The mixture was stirred at 80 C for 24 h. The solution was diluted in Et2O (10 mL), filtered on a short pad of silica, washed with Et2O (3 × 10 mL), and concentrated to dryness under reduced pressure. The residue was purified with a flash purification system to give the coupling product (Tables 1 and 2).

Reference： [1]Synthesis,2013,vol. 45,p. 2949 - 2958

33
[ 106-33-2 ]
[ 42882-31-5 ]
[ 946113-79-7 ]
[ 74496-21-2 ]

Yield	Reaction Conditions	Operation in experiment
37%	With 1-hydroxytetraphenyl-cyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-mu-hydrotetracarbonyldiruthenium(II); at 120℃; under 0.375038 Torr; for 48h;Enzymatic reaction;	General procedure: General experimental conditions and results on the DKR reactions are collected in Table2. First, 110mg (1mol%) of the Shvo's catalyst, 70ml of the corresponding glyme, racemic 1-(aryl)ethylamine and the corresponding acyl donor were placed in a three-necked 100ml round-bottom flask, equipped with a thermometer, a magnetic stirrer bar, a capillar and a Soxhlet head (50ml) with a reflux condenser. The enzyme (Novozyme 435) was packed in 4 porous polyethylene bags, 50mg in each. In the case of the slower reacting 1-(naphthyl)ethylamine, 6 bags containing 300mg of enzyme in total were utilized. The bags containing the enzyme were placed into an extraction chamber of the Soxhlet extractor together with 5mm glass beads. In this way the ?dead volume? of the Soxhlet extractor was reduced to approximately 20ml. Disposable thermo-sensors were placed between the enzyme bags. If desired, with proper construction of the reflux condenser, a thermometer could also be inserted into the glass beads. The outlet of the reflux condenser was connected to an inlet of a membrane pump equipped with vacuum control unit. The argon inlet was connected to the capillar and to the gas inlet of the pump. We recommend the incorporation of a 1-2l buffer flask between the apparatus and the vacuum pump for controlling the vacuum oscillation. The use of Teflon thermostable grease for the hot joints is likewise recommended. The side arm of the extractor should be thermally insulated. Loops of rubber tubing with cooling water circulation can be applied around the extraction chamber for additional cooling of the enzyme.

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 760,p. 161 - 166

34
[ 144-19-4 ]
[ 106-33-2 ]
C₂₀H₄₀O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1-hydroxytetraphenyl-cyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-mu-hydrotetracarbonyldiruthenium(II); at 105℃; under 97.5098 Torr; for 48h;	General procedure: General experimental conditions and results on the DKR reactions are collected in Table2. First, 110mg (1mol%) of the Shvo's catalyst, 70ml of the corresponding glyme, racemic 1-(aryl)ethylamine and the corresponding acyl donor were placed in a three-necked 100ml round-bottom flask, equipped with a thermometer, a magnetic stirrer bar, a capillar and a Soxhlet head (50ml) with a reflux condenser. The enzyme (Novozyme 435) was packed in 4 porous polyethylene bags, 50mg in each. In the case of the slower reacting 1-(naphthyl)ethylamine, 6 bags containing 300mg of enzyme in total were utilized. The bags containing the enzyme were placed into an extraction chamber of the Soxhlet extractor together with 5mm glass beads. In this way the ?dead volume? of the Soxhlet extractor was reduced to approximately 20ml. Disposable thermo-sensors were placed between the enzyme bags. If desired, with proper construction of the reflux condenser, a thermometer could also be inserted into the glass beads. The outlet of the reflux condenser was connected to an inlet of a membrane pump equipped with vacuum control unit. The argon inlet was connected to the capillar and to the gas inlet of the pump. We recommend the incorporation of a 1-2l buffer flask between the apparatus and the vacuum pump for controlling the vacuum oscillation. The use of Teflon thermostable grease for the hot joints is likewise recommended. The side arm of the extractor should be thermally insulated. Loops of rubber tubing with cooling water circulation can be applied around the extraction chamber for additional cooling of the enzyme.

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 760,p. 161 - 166

35
[ 106-33-2 ]
6-(N-(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl)succinylamido-6I-deoxy-2I,3I-di-Omethyl-hexakis(2II-VII, 3 II-VII, 6II-VII-tri-O-methyl)cyclomaltoheptaose [ No CAS ]
6-(N-(1-dodecanoyloxy-(2S,3S,4R)-dihydroxyoctadecan-2-yl)succinamido)-6I-deoxy-2I,3I-di-O-methyl-hexakis(2II-VII, 3 II-VII, 6II-VII-tri-O-methyl)cyclomaltoheptaose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With lipozyme; at 50℃; for 8h;Green chemistry; Enzymatic reaction;	General procedure: To a solution of 100 mg of compound 3 (55 mumol, 1 equiv) in 2 ml of corresponding fatty ester (excess), 100 mg of Lipozyme was added. The reaction was set under rotary evaporator at 50 C during 8 to 14 hours depending on the corresponding fatty ester. Lipozyme was filtered, and the solution was purified directly on silica gel (from pure EtOAc to EtOAc/MeOH 4:1(v/v)), giving white solid. Yields: 4 (80mg): 74%, 5 (75mg): 68%, 6 (72mg): 64%, 7 (69mg): 60%.

Reference： [1]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 2654 - 2657

36
[ 106-33-2 ]
[ 74-88-4 ]
[ 32836-44-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With magnesium; In diethyl ether; at 25℃; for 48h;Inert atmosphere;	General procedure: GaldenHT135/200 = 1:1 (2 mL) was placed in a test tube(13 mm Phi × 105 mm), to which MeI (571 mg, 4.0 mmol) wasadded slowly using a glass pipette under argon. Anhydrous Et2O(1 mL) was added slowly, whereupon three layers formed. Mgpowder (98 mg, 4.0 mmol) was then added slowly, and floatedbetween the Galden and ether layers, whereupon four layersformed. Subsequently, a solution of 2-decanone (1a, 313 mg, 2.0mmol) in anhydrous Et2O (3 mL) was added to the ether layer.The bottom layer was stirred slowly at 25 C for 2 d, taking carenot to mix the four layers. The ether solution and Mg salt weretaken into a flask, to which hydrochloric acid (2 M) was addedto quench the reaction, while cooling in an ice bath. The organiclayer was separated, and the aqueous layer was extracted withEt2O. The organic layer was collected, dried over Na2SO4, andconcentrated. The residue was purified by column chromatographyon silica gel (hexane-Et2O, 3:1) to give 2-methyl-2-decanol (2a)

Reference： [1]Synlett,2015,vol. 26,p. 1276 - 1280

37
[ 106-33-2 ]
[ 75-03-6 ]
[ 101433-18-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With magnesium; In diethyl ether; at 25℃; for 48h;Inert atmosphere;	General procedure: GaldenHT135/200 = 1:1 (2 mL) was placed in a test tube(13 mm Phi × 105 mm), to which MeI (571 mg, 4.0 mmol) wasadded slowly using a glass pipette under argon. Anhydrous Et2O(1 mL) was added slowly, whereupon three layers formed. Mgpowder (98 mg, 4.0 mmol) was then added slowly, and floatedbetween the Galden and ether layers, whereupon four layersformed. Subsequently, a solution of 2-decanone (1a, 313 mg, 2.0mmol) in anhydrous Et2O (3 mL) was added to the ether layer.The bottom layer was stirred slowly at 25 C for 2 d, taking carenot to mix the four layers. The ether solution and Mg salt weretaken into a flask, to which hydrochloric acid (2 M) was addedto quench the reaction, while cooling in an ice bath. The organiclayer was separated, and the aqueous layer was extracted withEt2O. The organic layer was collected, dried over Na2SO4, andconcentrated. The residue was purified by column chromatographyon silica gel (hexane-Et2O, 3:1) to give 2-methyl-2-decanol (2a)

Reference： [1]Synlett,2015,vol. 26,p. 1276 - 1280

38
[ 64-17-5 ]
[ 2146-71-6 ]
[ 106-33-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With carbon dioxide; at 46.02℃; under 66081.6 Torr; for 3.5h;High pressure; Supercritical conditions; Green chemistry;	General procedure: The enzymatic synthesis of citronellyl laurate esters was carried out in 50 mL high pressure reactor vessel. The instrument was equipped with the pressure reading controller and regulator model JASCO-PU-2080-CO2 plus. At first, given amount of vinyl laurate was added followed by addition of given amount of citronellol in the 50 mL reaction vessel. Finally, the reaction was started by addition of immobilized PVA/CHI lipase and the reactor vessel was closed appropriately and assembled to SC-CO2 high pressure reactor. The liquid SC-CO2 was pumped inside the reactor vessel with a flowrate of 3.5 mL/min. The reaction was conducted at given pressure (MPa) and temperature (C) designed by RSM software for given period. After, the completion of reaction, the SC-CO2 was slowly depressurized through a thermostat restrictor having temperature 50C which leaves back the residual reaction mass inside the reactor by leaving CO2. The reaction mass was then analyzed using the Perkin-Elmer, Clarus-400 Gas Chromatography (GC) equipped with a flame ionizing detector (FID) and capillary column. The oven temperature of GC was kept at 90C for 4 min and then rises at 10C/min up to 240C. The product formed was also confirmed by the gas-chromatography-mass spectroscopy analysis (GC-MS) by Shimadzu QP-2010 instrument.

Reference： [1]Process Biochemistry,2015,vol. 50,p. 1224 - 1236

39
[ 106-33-2 ]
[ 1120-16-7 ]
[ 2437-25-4 ]

Yield	Reaction Conditions	Operation in experiment
12%; 78%	With diisobutylaluminium hydride; ammonium chloride; In tetrahydrofuran; at 66℃; for 16h;Inert atmosphere;	General procedure: The solution of aminoalane reagent (prepared from 20 equiv. DIBAL-H in case of ester and lactonesubstrates or from 40 equiv. in case of carboxylic acid and amide substrates) was added to a solutionof carboxylic acid (1 eqiuv.) or its derivative (lactone, ester or amide, 1 equiv.) in anhydrous THF atroom temperature. Stirring was continued for 16 hours at 66 C. After this time, the reaction mixturewas cooled, quenched with aqueous solution of KHSO4 and the product was extracted with CHCl3.The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated. The crude product was purified by silica gel chromatography with hexane / ethyl acetateelution.

Reference： [1]Synlett,2015,vol. 26,p. 2288 - 2292

40
[ 106-33-2 ]
[ 693-23-2 ]

Yield	Reaction Conditions	Operation in experiment
	With alpha-D-glucopyranose; In water; at 35℃; for 134h;pH 5.8 - 6;Enzymatic reaction;	Example 2 Production of DDDA by an Engineered Mircoorganism (0056) A one milliliter frozen glycerol stock of Candida sp. strain sAA2178 (as disclosed in international patent application PCT/US2013/076664) was inoculated into a 500 ml baffled flask containing about 80 ml of SP92 culture medium (recipe below) under sterile conditions and the flask was capped with a foam plug and placed on a shaker at 30 C. and 250 rpms for about 24 hours. This culture was used to inoculate three 500 ml baffled flask containing about 80 ml of SP92 culture medium to a starting optical density at 600 nm of 0.4 and incubated at 24 hours at about 30 C. and 250 rpm. Each culture was then used to inoculate 1.5 Liters of SP92 (75 g/L dextrose) to an initial optical density of 600 nm of 2 in a 2.5 L baffled flask and incubated for 24 hrs at about 30 C. and 250 rpms. (0057) These cultures were used to inoculate about 200 ml of 1.5×KA1 media containing about 40.5 g/L of dextrose in a 300 L working volume stir tank fermenter. The fermenter was kept at about 35 degrees Celsius, agitation was kept at about 400 rpm, the airflow was about 1 VVM and the pH was set at about 5.8 using NaOH as base. Once dextrose was depleted the pH was increased to 6.0, glucose and ethyl-laurate were each fed into the fermenter at about 1.35 g/L-h and 1.125 g/L-h respectively for the duration of the fermentation for the first twenty four hours. The feed of ethyl-laurate was increased to about 1.92 g/L and was run for an additional 110 hrs. The resulting broth had a concentration of dodecanedioic acid of about 135 g/L as determined by GC analysis. SP92 Culture Medium (Per Liter) Material (0058) [table-us-00003-en] YNB w/o amino acids 6.7 g Yeast Extract 3.0 g Ammonium Sulfate 3.0 g Potassium Phosphate, Monobasic 1.0 g Potassium Phosphate, Dibasic 1.0 g Antifoam 0.060 g DeKA-2 Culture Medium (Per Liter) (0059) [table-us-00004-en] Ammonium Sulfate 10.5 g Potassium Phosphate, Monobasic 7.65 g Magnesium Sulfate 1.54 g Calcium Sulfate Dihydrate 0.248 g Citric Acid Anhydrous 0.09 g Iron (II) Sulfate 0.06 g Glucose 40.5 g Biotin, 1000x 0.3 ml Trace elements, 100x (see below) 1.5 ml Deionized Water to 1 liter Trace Elements (0060) [table-us-00005-en] Boric Acid 0.900 g Cupric Sulfate 0.110 g Potassium Iodide 0.180 g Manganese Sulfate Monohydrate 0.806 g Sodium Molybdate 0.360 g Zinc Sulfate 0.720 g Deionized Water to 1 liter

Reference： [1]Patent: US2015/361024,2015,A1 .Location in patent: Paragraph 0056-0060

41
[ 30089-00-0 ]
[ 7425-53-8 ]
[ 106-33-2 ]

Reference： [1]ACS Catalysis,2016,vol. 6,p. 258 - 261

42
[ 106-33-2 ]
[ 112-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen at 349.84℃;

Reference： [1]Xu, Jilei; Li, Ning; Yang, Xiaofeng; Li, Guangyi; Wang, Aiqin; Cong, Yu; Wang, Xiaodong; Zhang, Tao [ACS Catalysis, 2017, vol. 7, # 9, p. 5880 - 5886]

43
[ 106-33-2 ]
[ 536-74-3 ]
[ 1450903-46-4 ]

Yield	Reaction Conditions	Operation in experiment
48%		General procedure: The following experimental procedure for the partial alkynylation of ethyl benzoate to 1,3-diphenylprop-2-yn-1-one is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with phenyl acetylene (0.45 mL, 4.1 mmol) and THF (10 mL). After cooling to 0 C, n-BuLi (1.6 mL, 2.5 M in hexane, 4.0 mmol) was added dropwise and stirred for 1 h at room temperature. To the reaction mixture was slowly added morpholine (0.08 mL, 1.0 mmol) and stirred for 30 min at 0 C. Then, ethyl benzoate (0.14 mL, 1.0 mmol) was added and the mixture was stirred for 6 h again. The reaction was stopped by aqueous NH4Cl (aq) (10 mL) and extracted with diethyl ether (2 * 10 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel yielded 1,3-diphenylprop-2-yn-1-one (175 mg, 85%). All products in Table 2 were confirmed by comparison with NMR data reported of authentic sample.7

Reference： [1]Bulletin of the Korean Chemical Society,2018,vol. 39,p. 683 - 686

44
[ 78-83-1 ]
[ 106-33-2 ]
isobutyl dodecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With iodine; for 8h;Inert atmosphere; Reflux;	General procedure: In a typical experiment, in a 2-neck round-bottom flask, equipped with a reflux condenser, one equivalent of the corresponding acid or ester was dissolved in the opportune alcohol (0.60mL/mmol), and 2 or 4% of Iodine were added. The solution was let stirring at reflux and monitored by GC until complete conversion. The crude solution was concentrated at reduced pressure and treated with a saturated solution of Na2S2O3. The aqueous phase was then extracted three times with diethyl ether and the reunited organic fractions were washed with deionized water. The solution was dried over sodium sulfate, filtered and concentrated under reduced pressure. The obtained crude was then purified by flash chromatography.

Reference： [1]Tetrahedron,2018,vol. 74,p. 4381 - 4389

45
[ 106-33-2 ]
[ 3262-03-1 ]
[ 19397-74-1 ]

Yield	Reaction Conditions	Operation in experiment
66.3%	With sodium ethanolate; In ethanol; at 0 - 20℃;	Ethyl decylacetate (0.94 g, 7.8 mmol) was added to a solution of sodium ethoxide (1.1 g, 15.6 mmol) in dry ethanol (8 mL) at 0 C. The compound obtained by the method (1.5 g, 7.8 mmol) was added dropwise to the above reaction mixture, and the mixture was stirred at room temperature overnight. After refluxing for half an hour, it was poured into cold brine and extracted with EA (3 X 60 mL). Wash with saturated brine (2×50 mL), dry over anhydrous sodium The crude product is recrystallized from ethanol.1.3 g of a yellow solid was obtained in a yield of 66.3 %.

Reference： [1]Patent: CN108727416,2018,A .Location in patent: Paragraph 0335; 0336; 0337

46
[ 99-20-7 ]
[ 106-33-2 ]
trehalose monododecanoate [ No CAS ]
6,6’-O-didodecanoyl-α,α’-trehalose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: TREHALOSE With novozyme 435 In water at 80℃; Green chemistry; Enzymatic reaction; Stage #2: ethyl laurate In diethyl ether Green chemistry;	2.2. General synthesis of sugar esters General procedure: Enzymatic synthesis of sugar esters under solvent-free conditionswas carried out using a modified method from Gelo-Pujic et al. [23].The sugar substrate (1 mmol) was dissolved in 2 mL of water in a 50 mLround bottle and then impregnated on Novozyme 435 (0.034, 0.17,0.34 and 0.68 g/mol of sugar substrate) by evaporating the aqueoussolution under a reduced pressure by heating in a water bath. Here, awater bath temperature of up to 80 °C was used.The lipid substrate (La or LaEt) (1, 2, 3 or 4 mmol) dissolved indiethyl ether (Et2O) was added to the dried mixture. Here, adding LaEtwithout Et2O was also tried for a comparative study. The Et2O in thereaction mixture was evaporated completely prior to starting the reaction.The content in the oil bath was heated at different temperatures(50, 60, 70, 80, 90, 100, 110, 120, 130 and 150 °C) and monitored forvarious reaction times (6, 12, 24, 48, 72 and 96 h). After the reactionmixtures were cooled down to ambient temperatures, they were extracted by N,N-dimethylformamide (DMF) at 60 °C under ultrasonicationtreatment. Some sugar esters such as trehalose monoester(TME), trehalose diester (TDE) and glucose monoester (GME) wereisolated via silica gel column chromatography using a mixed solventsystem [chloroform/methanol/acetone/water=9/4/4/1 (v/v/v/v)] asan eluent. The nuclear magnetic resonance (NMR) spectra of TME, TDEand GME were consistent with the reported data for 6-O-lauroyl trehalose,6,6′-O-dilauroyl trehalose and 6-O-lauroyl-α-D-glucopyranose[30-32] (Figure S1, Supplementary Material), and the obtained sampleswere of high purity.

Reference： [1]Ogawa, Shigesaburo; Endo; Kitahara; Yamagishi, Takayuki; Aoyagi, Satoka; Hara, Setsuko [Carbohydrate Research, 2019, vol. 482]

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