[ CAS No. 2052-15-5 ] {[proInfo.proName]}

Name: 2052-15-5|Butyl 4-oxopentanoate|95%
Brand: Ambeed
SKU: A133151
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2D 3D

Structure of 2052-15-5 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 2052-15-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2052-15-5 ]

SDS Specification

Alternatived Products of [ 2052-15-5 ]

Product Details of [ 2052-15-5 ]

CAS No. :	2052-15-5	MDL No. :	MFCD00009449
Formula :	C₉H₁₆O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ISBWNEKJSSLXOD-UHFFFAOYSA-N
M.W :	172.22	Pubchem ID :	16331
Synonyms :

Calculated chemistry of [ 2052-15-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.78
Num. rotatable bonds :	7
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.86
TPSA :	43.37 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.11
Log Po/w (XLOGP3) :	0.96
Log Po/w (WLOGP) :	1.7
Log Po/w (MLOGP) :	1.29
Log Po/w (SILICOS-IT) :	1.97
Consensus Log Po/w :	1.61

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.05
Solubility :	15.3 mg/ml ; 0.089 mol/l
Class :	Very soluble
Log S (Ali) :	-1.46
Solubility :	6.0 mg/ml ; 0.0348 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.31
Solubility :	0.84 mg/ml ; 0.00488 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 2052-15-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2052-15-5 ]

* 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 [ 2052-15-5 ]
Downstream synthetic route of [ 2052-15-5 ]

[ 2052-15-5 ] Synthesis Path-Upstream 1~1

1
[ 2052-15-5 ]
[ 71-36-3 ]
[ 2050-60-4 ]
[ 141-03-7 ]

Yield	Reaction Conditions	Operation in experiment
79.9%	Stage #1: at 120℃; for 6 h; Autoclave Stage #2: at 20℃; for 8 h;	To a 35 mL autoclave, 0.43 g of n-butyl levulinate and 2.5 molpercent of n-butyl levulinate were added to 2 mL of dimethyl sulfoxide, and oxygen was charged to 0.10 MPa , 0.5MPa, 1.0MPa, 1.5MPa, 2.0MPa, stirring constantly heated to 120 ° C and maintained for 6h. And then cooled to room temperature. The whole product was transferred to a round bottom flask, 20 mL of n-butanol and 0.15 g of phosphotungstic acid were added, heated to reflux for 8 h, and cooled to room temperature. The product was analyzed by the method of Example 1 to give the conversion of n-butyl levulinate and the product di-n-butyl succinate selectivity as shown in Table I.

Reference： [1] Patent: CN103539665, 2016, B, . Location in patent: Paragraph 0063-0066

[ 2052-15-5 ] Synthesis Path-Downstream 1~88

1
[ 98-00-0 ]
[ 71-36-3 ]
[ 2052-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	sulfuric acid; In butyl levulinate; water; at 130℃; for 2.08333h;Product distribution / selectivity;	Example 5; The procedure of Example 1 was repeated with n-butyl levulinate (obtained from the Langfang Triple Well Chemicals Company, Ltd. of Langfang City, HeBei, China) and n-butanol (99.9%, obtained from the Sigma-Aldrich Company of St.Louis, MO). Table 2 shows the recorded boiling points of the mixtures.Table 2. Boiling points of n-butanol/n-butyl levulinate mixtures.A 500 rnL three-neck flask equipped with a magnetic stir bar, a dropping funnel, a condenser, and a thermocouple was charged with 100.04g (0.581mol) n- butyl levulinate (obtained from the Langfang Triple Well Chemicals Company, Ltd. of Langfang City, HeBei, China), 20.84g (0.281 mol) n-butanol (99.9%, obtained from the Sigma-Aldrich Company of St. Louis, MO), 1.463 mL deionized water, and 0.575 mL cone, sulfuric acid. The mixture was heated with a heating mantle to a temperature of 1300C. A mixture of 49.07g (0.495 mol) furfuryl alcohol (99%, obtained from Acros Organics of Geel, Belgium) and 55.0Og (0.742 mol) n-butanol was added to the reaction mixture dropwise over about 65 minutes. The reaction temperature was maintained at 1300C for additional 1 hour after addition was complete. Then the reaction flask was allowed to cool to room temperature. The crude reaction mixture appeared to be homogeneous, with no insoluble or phase- separated material observed. About 50.1O g of the reaction mixture was transferred to a 250 mL flask and distilled using a Kugelrohr apparatus at about 7-10 Torr and an air bath temperature of up to 1810C.After distillation, total amount of undistillable solid left in the flask was 1.43 g, which contained 0.23 g sulfuric acid and 1.20 g of a tarry residue. The ratio of the amount of tarry residue to the amount of furfuryl alcohol added was measured to be 11.1 wt%. GC-MS analysis of the crude reaction product was carried out as for Example 2 and showed that n-butyl levulinate was present at 98.0% based on peak area.
	With silica-alumina; at 180℃;	General procedure: The catalytic activity experiments were conducted in a fixed bed quartz reactor (14 mm id and 280 mm length)at atmospheric pressure. In each catalytic experiment, 250 mg of catalyst is diluted with equal amount of quartz particles and placed at the centre of the reactor. Priorto the reaction, the catalyst was flushed in a N2 flow of1800 mL h-1 at 180 C for 1 h. The liquid feed withrequired molar ratio of FAL to alcohol was continuouslyfed at a liquid hour space velocity (LHSV) of 1 h-1 usinga feed pump (M/s. B. Braun Co., Germany). Unless otherwisespecified the reaction conditions are same. The liquidproduct mixture was collected in an ice cold trap andanalyzed at regular intervals. This product mixture wasanalyzed by a flame ionization detector (FID) equippedgas chromatograph, GC-17A (M/s. Shimadzu Instruments,Japan) with EB-5 capillary column (30 m × 0.53 mm ×5.0 mum) and the product components were confirmed byusing GC-MS, QP-2010 (M/s. Shimadzu Instruments, Japan) with EB-5 MS capillary column (30 m × 0.25 mm× 0.25 mum).

Reference： [1]Catalysis Communications,2019,vol. 123,p. 109 - 113
[2]ChemSusChem,2011,vol. 4,p. 112 - 118
[3]Green Chemistry,2014,vol. 16,p. 1436 - 1443
[4]ChemCatChem,2014,vol. 6,p. 3080 - 3083
[5]RSC Advances,2016,vol. 6,p. 22174 - 22178
[6]Molecular catalysis,2020,vol. 488
[7]RSC Advances,2016,vol. 6,p. 90232 - 90238
[8]Patent: WO2018/112779,2018,A1 .Location in patent: Page/Page column 11
[9]Patent: WO2010/102203,2010,A2 .Location in patent: Page/Page column 24-25
[10]Green Chemistry,2013,vol. 15,p. 3367 - 3376
[11]Catalysis Letters,2018,vol. 148,p. 1731 - 1738
[12]Patent: US2763665,1952,
[13]Patent: US2763665,1952,
[14]New Journal of Chemistry,2019,vol. 43,p. 14694 - 14700

2
[ 591-12-8 ]
[ 71-36-3 ]
[ 88928-51-2 ]
[ 2052-15-5 ]

Reference： [1]Catalysis science and technology,2015,vol. 5,p. 5168 - 5173
[2]Catalysis science and technology,2015,vol. 5,p. 5168 - 5173
[3]Patent: US2493676,1947,

3
[ 102-71-6 ]
[ 2052-15-5 ]
[ 86240-21-3 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 3080

4
[ 597-09-1 ]
[ 2052-15-5 ]
[ 145277-24-3 ]

Reference： [1]Patent: US2406504,1944,

5
[ 2052-15-5 ]
[ 6316-04-7 ]
[ 114597-86-3 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1955,vol. 28,p. 54,56

6
[ 2052-15-5 ]
[ 75-16-1 ]
[ 3123-97-5 ]

Reference： [1]Journal of the American Chemical Society,1940,vol. 62,p. 2619

7
[ 2052-15-5 ]
[ 63543-02-2 ]
[ 102449-25-2 ]

Reference： [1]Journal of the American Chemical Society,1957,vol. 79,p. 1680

8
[ 2052-15-5 ]
4-oxo-pent-2<i>t</i>(?)-enoic acid butyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1950,vol. 72,p. 3296

9
[ 2052-15-5 ]
[ 129549-67-3 ]

Reference： [1]Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry,1957,vol. 60,p. 282,285
Chem.Abstr.,1959,p. 8105

10
[ 2052-15-5 ]
4-phenylhydrazono-valeric acid butyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1930,vol. 52,p. 4883

11
[ 2052-15-5 ]
[ 2065-66-9 ]
[ 999-24-6 ]

Reference： [1]Journal of Organometallic Chemistry,1965,vol. 3,p. 101 - 106

12
[ 2052-15-5 ]
[ 94712-75-1 ]

Reference： [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 2781 - 2785
Zhurnal Obshchei Khimii,1962,vol. 32,p. 2823 - 2828

13
[ 2052-15-5 ]
[ 129549-67-3 ]

Reference： [1]Synthetic Communications,1990,vol. 20,p. 999 - 1010

14
[ 141-32-2 ]
[ 75-07-0 ]
[ 2052-15-5 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 3063 - 3066

15
[ 2052-15-5 ]
5-Bromo-4-oxo-pentanoic acid butyl ester [ No CAS ]
3-Bromo-4-oxo-pentanoic acid butyl ester [ No CAS ]

Reference： [1]Synthetic Communications,1994,vol. 24,p. 2557 - 2562
[2]Synthetic Communications,1994,vol. 24,p. 2557 - 2562

16
[ 624-45-3 ]
[ 71-36-3 ]
[ 2052-15-5 ]

Reference： [1]Synthetic Communications,2001,vol. 31,p. 289 - 294
[2]Tetrahedron Letters,1996,vol. 37,p. 233 - 236
[3]Molecular catalysis,2020,vol. 483

17
[ 2052-15-5 ]
[ 105-56-6 ]
[ 917087-84-4 ]

Yield	Reaction Conditions	Operation in experiment
40.1%	With sulfur; In ethanol; diethylamine; at 20℃;	A mixture of 1.72 g of <strong>[2052-15-5]butyl 4-oxopentanoate</strong>, 352 mg of sulfur, 1.13 g of ethyl cyanoacetate, 5 mL of ethanol and 1 mL of diethylamine was stirred at room temperature overnight. Chloroform was added to the reaction mixture, followed by washing with saturated aqueous sodium bicarbonate solution, drying over anhydrous magnesium sulfate and removal of the solvent by distillation under reduced pressure. The residue was purified on silica gel column chromatography (hexane: ethyl acetate = 3:1) to provide 1.20 g (40.1%) of the title compound. 1H-NMR(CDCl3) delta:0.9-1.0(3H,m),1.3-1.5(5H,m),1.5-1.7(2H,m), 2.19(3H,s),2.5-2.6(2H,m),2.7-2.8(2H,m),4.0-4.2(2H,m) MS(m/z):299(M+),198(base)

Reference： [1]Patent: EP1908765,2008,A1 .Location in patent: Page/Page column 22

18
[ 2052-15-5 ]
5-butyloxymethyl-furfural [ No CAS ]
1,1,1,6,6,6-hexafluoro-5-hydroxy-5-methyl-hexan-2-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 1436 - 1440

19
[ 106-98-9 ]
[ 64-18-6 ]
[ 123-76-2 ]
[ 592-84-7 ]
[ 2052-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	sulfuric acid; In water; at 100℃; under 5175.52 Torr; for 2h;Conversion of starting material;	A 5 cc autoclave is charged with 2 cc of an aqueous solution containing 2 mmoles of levulinic acid and 2 mmoles of formic acid. 5 wt. % sulfuric acid is added as a catalyst. The reactor is pressurized to 0.69 MPa with 1-butene and heated to 100 C. for 2 hours while maintaining a constant pressure of 1-butene. After cooling, the organic phase is separated. A mixture of butyl formate and butyl levulinate is formed as product.
	percent ZSM-5 zeolite; In water; at 100℃; under 5175.52 Torr; for 4h;Conversion of starting material;	A 5 cc autoclave is charged with 2 cc of an aqueous solution containing 0.5 mmoles of levulinic acid and 2 mmoles of formic acid. 15 wt. % ZSM-5 zeolite is added as a catalyst. The reactor is pressurized to 0.69 MPa with 1-butene and heated to 100 C. for 4 hours while maintaining a constant pressure of 1-butene. After cooling, the organic phase is separated. A mixture of butyl formate and butyl levulinate is formed as product.
	ZSM-5 zeolite; trifluorormethanesulfonic acid; In water; at 100℃; under 5175.52 Torr; for 0.5h;Conversion of starting material;	A 5 cc autoclave is charged with 2 cc of an aqueous solution containing 2 mmoles of levulinic acid and 0.5 mmoles of formic acid. 2 wt. % triflic acid is added as a catalyst. The reactor is pressurized to 0.69 MPa with 1-butene and heated to 100 C. for 0.5 hours while maintaining a constant pressure of 1-butene. After cooling, the organic phase is separated. A mixture of butyl formate and butyl levulinate is formed as product.

	sulfuric acid; In n-heptane; water; at 150℃; under 5175.52 Torr; for 0.5h;Conversion of starting material;	A 5 cc autoclave is charged with 1 cc of heptane and 1 cc of an aqueous solution containing 2 mmoles of levulinic acid and 2 mmoles of formic acid. 5 wt. % sulfuric acid is added as a catalyst. The reactor is pressurized to 0.69 MPa with 1-butene and heated to 150 C. for 0.5 hours while maintaining a constant pressure of isobutene. After cooling, the organic phase is separated. A mixture of butyl formate and butyl levulinate is formed as product.
	sulfuric acid; In 2,2,4-trimethylpentane; water; at 100℃; under 5175.52 Torr; for 2h;Conversion of starting material;	A 5 cc autoclave is charged with 1 cc of iso-octane and 1 cc of an aqueous solution containing 2 mmoles of levulinic acid and 2 mmoles of formic acid. 5 wt. % sulfuric acid is added as a catalyst. The reactor is pressurized to 0.69 MPa with 1-butene and heated to 100 C. for 2 hours while maintaining a constant pressure of 1-butene. After cooling, the organic phase is separated. A mixture of butyl formate and butyl levulinate is formed as product.

Reference： [1]Patent: US2003/233011,2003,A1 .Location in patent: Page 6
[2]Patent: US2003/233011,2003,A1 .Location in patent: Page 6
[3]Patent: US2003/233011,2003,A1 .Location in patent: Page 6
[4]Patent: US2003/233011,2003,A1 .Location in patent: Page 6
[5]Patent: US2003/233011,2003,A1 .Location in patent: Page 6

20
[ 591-12-8 ]
[ 71-36-3 ]
[ 2052-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	triethylamine; at 100 - 150℃; under 41404.1 Torr; for 1 - 3h;Product distribution / selectivity;	Example 1 General Procedure for the Reaction of Alcohols and alpha-Angelica Lactone A 2 cc pressure vessel was charged with 700 mg of a solution consisting of alcohol, alpha-angelica lactone and 50 mg of a catalyst. The reactor was pressurized with nitrogen and heated to reactor temperature for a specified period of time. The vessel was then cooled, vented and the products analyzed by gas chromatography on a HP-6890 GC (Agilent Technologies; Palo Alto, Calif.) and HP-5972A GC-MS detector equipped with a 25M×0.25MM ID CP-Wax 58 (FFAP) column. The GC yields were obtained by adding methoxyethyl ether as the internal standard. The examples described below were performed according to a similar procedure under the conditions indicated for each example.; Examples 2-19 Reaction of alpha-Angelica Lactone (AGL) with 1-Butanol (1-BuOH) to Produce Butyl Levulinate (BuLV) N2 AGL BuLV Expt. Time Temp Pressure Conversion Selectivity No. Basic Catalyst (hrs) ( C.) (MPag) Feedstock (%) (%) 2Et3N 3 100 5.52 AGL (30%)/1- 77.56 29.08 BuOH (70%) 3Et3N 1 150 5.52 AGL (30%)/1- 89.03 45.68 BuOH (70%) 4Et3N 3 150 5.52 AGL (30%)/1- 98.88 51.31 BuOH (70%) 5 Dabco 3 150 5.52 AGL (30%)/1- 99.22 58.01 BuOH (70%) 6 20% 3 150 5.52 AGL (30%)/1- 96.97 55.68 CsOAc/KA-160 BuOH (70%) SiO2 7 20% 3 150 5.52 AGL (30%)/1- 98.96 53.36 RbOAc/KA-160 BuOH (70%) SiO2 8 20% 1 150 5.52 AGL (30%)/1- 91.87 37.56 CsOAc/KA-160 BuOH (70%) SiO2 9 20% 1 150 5.52 AGL (30%)/1- 95.42 42.01 RbOAc/KA-160 BuOH (70%) SiO2 10 20% 3 100 5.52 AGL (30%)/1- 62.59 20.94 CsOAc/KA-160 BuOH (70%) SiO2 11 20% 3 100 5.52 AGL (30%)/1- 63.21 21.98 RbOAc/KA-160 BuOH (70%) SiO2 12Li2CO3 3 100 5.52 AGL (30%)/1- 22.52 79.06 BuOH (70%) 13Na2CO3 3 100 5.52 AGL (30%)/1- 71.73 32.81 BuOH (70%) 14K2CO3 3 100 5.52 AGL (30%)/1- 59.17 62.23 BuOH (70%) 15Sc2CO3 3 100 5.52 AGL (30%)/1- 33.81 64.46 BuOH (70%) 16Li2CO3 1 150 5.52 AGL (30%)/1- 62.91 82.62 BuOH (70%) 17Na2CO3 1 150 5.52 AGL (30%)/1- 97.30 68.86 BuOH (70%) 18K2CO3 1 150 5.52 AGL (30%)/1- 97.65 65.32 BuOH (70%) 19Sc2CO3 1 150 5.52 AGL (30%)/1- 79.92 70.51 BuOH (70%)
	potassium carbonate; at 100 - 150℃; under 41404.1 Torr; for 1 - 3h;Product distribution / selectivity;	Example 1 General Procedure for the Reaction of Alcohols and alpha-Angelica Lactone A 2 cc pressure vessel was charged with 700 mg of a solution consisting of alcohol, alpha-angelica lactone and 50 mg of a catalyst. The reactor was pressurized with nitrogen and heated to reactor temperature for a specified period of time. The vessel was then cooled, vented and the products analyzed by gas chromatography on a HP-6890 GC (Agilent Technologies; Palo Alto, Calif.) and HP-5972A GC-MS detector equipped with a 25M×0.25MM ID CP-Wax 58 (FFAP) column. The GC yields were obtained by adding methoxyethyl ether as the internal standard. The examples described below were performed according to a similar procedure under the conditions indicated for each example.; Examples 2-19 Reaction of alpha-Angelica Lactone (AGL) with 1-Butanol (1-BuOH) to Produce Butyl Levulinate (BuLV) N2 AGL BuLV Expt. Time Temp Pressure Conversion Selectivity No. Basic Catalyst (hrs) ( C.) (MPag) Feedstock (%) (%) 2Et3N 3 100 5.52 AGL (30%)/1- 77.56 29.08 BuOH (70%) 3Et3N 1 150 5.52 AGL (30%)/1- 89.03 45.68 BuOH (70%) 4Et3N 3 150 5.52 AGL (30%)/1- 98.88 51.31 BuOH (70%) 5 Dabco 3 150 5.52 AGL (30%)/1- 99.22 58.01 BuOH (70%) 6 20% 3 150 5.52 AGL (30%)/1- 96.97 55.68 CsOAc/KA-160 BuOH (70%) SiO2 7 20% 3 150 5.52 AGL (30%)/1- 98.96 53.36 RbOAc/KA-160 BuOH (70%) SiO2 8 20% 1 150 5.52 AGL (30%)/1- 91.87 37.56 CsOAc/KA-160 BuOH (70%) SiO2 9 20% 1 150 5.52 AGL (30%)/1- 95.42 42.01 RbOAc/KA-160 BuOH (70%) SiO2 10 20% 3 100 5.52 AGL (30%)/1- 62.59 20.94 CsOAc/KA-160 BuOH (70%) SiO2 11 20% 3 100 5.52 AGL (30%)/1- 63.21 21.98 RbOAc/KA-160 BuOH (70%) SiO2 12Li2CO3 3 100 5.52 AGL (30%)/1- 22.52 79.06 BuOH (70%) 13Na2CO3 3 100 5.52 AGL (30%)/1- 71.73 32.81 BuOH (70%) 14K2CO3 3 100 5.52 AGL (30%)/1- 59.17 62.23 BuOH (70%) 15Sc2CO3 3 100 5.52 AGL (30%)/1- 33.81 64.46 BuOH (70%) 16Li2CO3 1 150 5.52 AGL (30%)/1- 62.91 82.62 BuOH (70%) 17Na2CO3 1 150 5.52 AGL (30%)/1- 97.30 68.86 BuOH (70%) 18K2CO3 1 150 5.52 AGL (30%)/1- 97.65 65.32 BuOH (70%) 19Sc2CO3 1 150 5.52 AGL (30%)/1- 79.92 70.51 BuOH (70%)
	1,4-diaza-bicyclo[2.2.2]octane; at 150℃; under 41404.1 Torr; for 3h;Product distribution / selectivity;	Example 1 General Procedure for the Reaction of Alcohols and alpha-Angelica Lactone A 2 cc pressure vessel was charged with 700 mg of a solution consisting of alcohol, alpha-angelica lactone and 50 mg of a catalyst. The reactor was pressurized with nitrogen and heated to reactor temperature for a specified period of time. The vessel was then cooled, vented and the products analyzed by gas chromatography on a HP-6890 GC (Agilent Technologies; Palo Alto, Calif.) and HP-5972A GC-MS detector equipped with a 25M×0.25MM ID CP-Wax 58 (FFAP) column. The GC yields were obtained by adding methoxyethyl ether as the internal standard. The examples described below were performed according to a similar procedure under the conditions indicated for each example.; Examples 2-19 Reaction of alpha-Angelica Lactone (AGL) with 1-Butanol (1-BuOH) to Produce Butyl Levulinate (BuLV) N2 AGL BuLV Expt. Time Temp Pressure Conversion Selectivity No. Basic Catalyst (hrs) ( C.) (MPag) Feedstock (%) (%) 2Et3N 3 100 5.52 AGL (30%)/1- 77.56 29.08 BuOH (70%) 3Et3N 1 150 5.52 AGL (30%)/1- 89.03 45.68 BuOH (70%) 4Et3N 3 150 5.52 AGL (30%)/1- 98.88 51.31 BuOH (70%) 5 Dabco 3 150 5.52 AGL (30%)/1- 99.22 58.01 BuOH (70%) 6 20% 3 150 5.52 AGL (30%)/1- 96.97 55.68 CsOAc/KA-160 BuOH (70%) SiO2 7 20% 3 150 5.52 AGL (30%)/1- 98.96 53.36 RbOAc/KA-160 BuOH (70%) SiO2 8 20% 1 150 5.52 AGL (30%)/1- 91.87 37.56 CsOAc/KA-160 BuOH (70%) SiO2 9 20% 1 150 5.52 AGL (30%)/1- 95.42 42.01 RbOAc/KA-160 BuOH (70%) SiO2 10 20% 3 100 5.52 AGL (30%)/1- 62.59 20.94 CsOAc/KA-160 BuOH (70%) SiO2 11 20% 3 100 5.52 AGL (30%)/1- 63.21 21.98 RbOAc/KA-160 BuOH (70%) SiO2 12Li2CO3 3 100 5.52 AGL (30%)/1- 22.52 79.06 BuOH (70%) 13Na2CO3 3 100 5.52 AGL (30%)/1- 71.73 32.81 BuOH (70%) 14K2CO3 3 100 5.52 AGL (30%)/1- 59.17 62.23 BuOH (70%) 15Sc2CO3 3 100 5.52 AGL (30%)/1- 33.81 64.46 BuOH (70%) 16Li2CO3 1 150 5.52 AGL (30%)/1- 62.91 82.62 BuOH (70%) 17Na2CO3 1 150 5.52 AGL (30%)/1- 97.30 68.86 BuOH (70%) 18K2CO3 1 150 5.52 AGL (30%)/1- 97.65 65.32 BuOH (70%) 19Sc2CO3 1 150 5.52 AGL (30%)/1- 79.92 70.51 BuOH (70%)

	sodium carbonate; at 100 - 150℃; under 41404.1 Torr; for 1 - 3h;Product distribution / selectivity;	Example 1 General Procedure for the Reaction of Alcohols and alpha-Angelica Lactone A 2 cc pressure vessel was charged with 700 mg of a solution consisting of alcohol, alpha-angelica lactone and 50 mg of a catalyst. The reactor was pressurized with nitrogen and heated to reactor temperature for a specified period of time. The vessel was then cooled, vented and the products analyzed by gas chromatography on a HP-6890 GC (Agilent Technologies; Palo Alto, Calif.) and HP-5972A GC-MS detector equipped with a 25M×0.25MM ID CP-Wax 58 (FFAP) column. The GC yields were obtained by adding methoxyethyl ether as the internal standard. The examples described below were performed according to a similar procedure under the conditions indicated for each example.; Examples 2-19 Reaction of alpha-Angelica Lactone (AGL) with 1-Butanol (1-BuOH) to Produce Butyl Levulinate (BuLV) N2 AGL BuLV Expt. Time Temp Pressure Conversion Selectivity No. Basic Catalyst (hrs) ( C.) (MPag) Feedstock (%) (%) 2Et3N 3 100 5.52 AGL (30%)/1- 77.56 29.08 BuOH (70%) 3Et3N 1 150 5.52 AGL (30%)/1- 89.03 45.68 BuOH (70%) 4Et3N 3 150 5.52 AGL (30%)/1- 98.88 51.31 BuOH (70%) 5 Dabco 3 150 5.52 AGL (30%)/1- 99.22 58.01 BuOH (70%) 6 20% 3 150 5.52 AGL (30%)/1- 96.97 55.68 CsOAc/KA-160 BuOH (70%) SiO2 7 20% 3 150 5.52 AGL (30%)/1- 98.96 53.36 RbOAc/KA-160 BuOH (70%) SiO2 8 20% 1 150 5.52 AGL (30%)/1- 91.87 37.56 CsOAc/KA-160 BuOH (70%) SiO2 9 20% 1 150 5.52 AGL (30%)/1- 95.42 42.01 RbOAc/KA-160 BuOH (70%) SiO2 10 20% 3 100 5.52 AGL (30%)/1- 62.59 20.94 CsOAc/KA-160 BuOH (70%) SiO2 11 20% 3 100 5.52 AGL (30%)/1- 63.21 21.98 RbOAc/KA-160 BuOH (70%) SiO2 12Li2CO3 3 100 5.52 AGL (30%)/1- 22.52 79.06 BuOH (70%) 13Na2CO3 3 100 5.52 AGL (30%)/1- 71.73 32.81 BuOH (70%) 14K2CO3 3 100 5.52 AGL (30%)/1- 59.17 62.23 BuOH (70%) 15Sc2CO3 3 100 5.52 AGL (30%)/1- 33.81 64.46 BuOH (70%) 16Li2CO3 1 150 5.52 AGL (30%)/1- 62.91 82.62 BuOH (70%) 17Na2CO3 1 150 5.52 AGL (30%)/1- 97.30 68.86 BuOH (70%) 18K2CO3 1 150 5.52 AGL (30%)/1- 97.65 65.32 BuOH (70%) 19Sc2CO3 1 150 5.52 AGL (30%)/1- 79.92 70.51 BuOH (70%)
	scandium carbonate; at 100 - 150℃; under 41404.1 Torr; for 1 - 3h;Product distribution / selectivity;	Example 1 General Procedure for the Reaction of Alcohols and alpha-Angelica Lactone A 2 cc pressure vessel was charged with 700 mg of a solution consisting of alcohol, alpha-angelica lactone and 50 mg of a catalyst. The reactor was pressurized with nitrogen and heated to reactor temperature for a specified period of time. The vessel was then cooled, vented and the products analyzed by gas chromatography on a HP-6890 GC (Agilent Technologies; Palo Alto, Calif.) and HP-5972A GC-MS detector equipped with a 25M×0.25MM ID CP-Wax 58 (FFAP) column. The GC yields were obtained by adding methoxyethyl ether as the internal standard. The examples described below were performed according to a similar procedure under the conditions indicated for each example.; Examples 2-19 Reaction of alpha-Angelica Lactone (AGL) with 1-Butanol (1-BuOH) to Produce Butyl Levulinate (BuLV) N2 AGL BuLV Expt. Time Temp Pressure Conversion Selectivity No. Basic Catalyst (hrs) ( C.) (MPag) Feedstock (%) (%) 2Et3N 3 100 5.52 AGL (30%)/1- 77.56 29.08 BuOH (70%) 3Et3N 1 150 5.52 AGL (30%)/1- 89.03 45.68 BuOH (70%) 4Et3N 3 150 5.52 AGL (30%)/1- 98.88 51.31 BuOH (70%) 5 Dabco 3 150 5.52 AGL (30%)/1- 99.22 58.01 BuOH (70%) 6 20% 3 150 5.52 AGL (30%)/1- 96.97 55.68 CsOAc/KA-160 BuOH (70%) SiO2 7 20% 3 150 5.52 AGL (30%)/1- 98.96 53.36 RbOAc/KA-160 BuOH (70%) SiO2 8 20% 1 150 5.52 AGL (30%)/1- 91.87 37.56 CsOAc/KA-160 BuOH (70%) SiO2 9 20% 1 150 5.52 AGL (30%)/1- 95.42 42.01 RbOAc/KA-160 BuOH (70%) SiO2 10 20% 3 100 5.52 AGL (30%)/1- 62.59 20.94 CsOAc/KA-160 BuOH (70%) SiO2 11 20% 3 100 5.52 AGL (30%)/1- 63.21 21.98 RbOAc/KA-160 BuOH (70%) SiO2 12Li2CO3 3 100 5.52 AGL (30%)/1- 22.52 79.06 BuOH (70%) 13Na2CO3 3 100 5.52 AGL (30%)/1- 71.73 32.81 BuOH (70%) 14K2CO3 3 100 5.52 AGL (30%)/1- 59.17 62.23 BuOH (70%) 15Sc2CO3 3 100 5.52 AGL (30%)/1- 33.81 64.46 BuOH (70%) 16Li2CO3 1 150 5.52 AGL (30%)/1- 62.91 82.62 BuOH (70%) 17Na2CO3 1 150 5.52 AGL (30%)/1- 97.30 68.86 BuOH (70%) 18K2CO3 1 150 5.52 AGL (30%)/1- 97.65 65.32 BuOH (70%) 19Sc2CO3 1 150 5.52 AGL (30%)/1- 79.92 70.51 BuOH (70%)
	20%CsOAc/KA-160 SiO2; at 100 - 150℃; under 41404.1 Torr; for 1 - 3h;Product distribution / selectivity;	Example 1 General Procedure for the Reaction of Alcohols and alpha-Angelica Lactone A 2 cc pressure vessel was charged with 700 mg of a solution consisting of alcohol, alpha-angelica lactone and 50 mg of a catalyst. The reactor was pressurized with nitrogen and heated to reactor temperature for a specified period of time. The vessel was then cooled, vented and the products analyzed by gas chromatography on a HP-6890 GC (Agilent Technologies; Palo Alto, Calif.) and HP-5972A GC-MS detector equipped with a 25M×0.25MM ID CP-Wax 58 (FFAP) column. The GC yields were obtained by adding methoxyethyl ether as the internal standard. The examples described below were performed according to a similar procedure under the conditions indicated for each example.; Examples 2-19 Reaction of alpha-Angelica Lactone (AGL) with 1-Butanol (1-BuOH) to Produce Butyl Levulinate (BuLV) N2 AGL BuLV Expt. Time Temp Pressure Conversion Selectivity No. Basic Catalyst (hrs) ( C.) (MPag) Feedstock (%) (%) 2Et3N 3 100 5.52 AGL (30%)/1- 77.56 29.08 BuOH (70%) 3Et3N 1 150 5.52 AGL (30%)/1- 89.03 45.68 BuOH (70%) 4Et3N 3 150 5.52 AGL (30%)/1- 98.88 51.31 BuOH (70%) 5 Dabco 3 150 5.52 AGL (30%)/1- 99.22 58.01 BuOH (70%) 6 20% 3 150 5.52 AGL (30%)/1- 96.97 55.68 CsOAc/KA-160 BuOH (70%) SiO2 7 20% 3 150 5.52 AGL (30%)/1- 98.96 53.36 RbOAc/KA-160 BuOH (70%) SiO2 8 20% 1 150 5.52 AGL (30%)/1- 91.87 37.56 CsOAc/KA-160 BuOH (70%) SiO2 9 20% 1 150 5.52 AGL (30%)/1- 95.42 42.01 RbOAc/KA-160 BuOH (70%) SiO2 10 20% 3 100 5.52 AGL (30%)/1- 62.59 20.94 CsOAc/KA-160 BuOH (70%) SiO2 11 20% 3 100 5.52 AGL (30%)/1- 63.21 21.98 RbOAc/KA-160 BuOH (70%) SiO2 12Li2CO3 3 100 5.52 AGL (30%)/1- 22.52 79.06 BuOH (70%) 13Na2CO3 3 100 5.52 AGL (30%)/1- 71.73 32.81 BuOH (70%) 14K2CO3 3 100 5.52 AGL (30%)/1- 59.17 62.23 BuOH (70%) 15Sc2CO3 3 100 5.52 AGL (30%)/1- 33.81 64.46 BuOH (70%) 16Li2CO3 1 150 5.52 AGL (30%)/1- 62.91 82.62 BuOH (70%) 17Na2CO3 1 150 5.52 AGL (30%)/1- 97.30 68.86 BuOH (70%) 18K2CO3 1 150 5.52 AGL (30%)/1- 97.65 65.32 BuOH (70%) 19Sc2CO3 1 150 5.52 AGL (30%)/1- 79.92 70.51 BuOH (70%)
	20% Rb(acetate) supported on Engelhard KA-160 SiO2; at 100 - 150℃; under 41404.1 Torr; for 1 - 3h;Product distribution / selectivity;	Example 1 General Procedure for the Reaction of Alcohols and alpha-Angelica Lactone A 2 cc pressure vessel was charged with 700 mg of a solution consisting of alcohol, alpha-angelica lactone and 50 mg of a catalyst. The reactor was pressurized with nitrogen and heated to reactor temperature for a specified period of time. The vessel was then cooled, vented and the products analyzed by gas chromatography on a HP-6890 GC (Agilent Technologies; Palo Alto, Calif.) and HP-5972A GC-MS detector equipped with a 25M×0.25MM ID CP-Wax 58 (FFAP) column. The GC yields were obtained by adding methoxyethyl ether as the internal standard. The examples described below were performed according to a similar procedure under the conditions indicated for each example.; Examples 2-19 Reaction of alpha-Angelica Lactone (AGL) with 1-Butanol (1-BuOH) to Produce Butyl Levulinate (BuLV) N2 AGL BuLV Expt. Time Temp Pressure Conversion Selectivity No. Basic Catalyst (hrs) ( C.) (MPag) Feedstock (%) (%) 2Et3N 3 100 5.52 AGL (30%)/1- 77.56 29.08 BuOH (70%) 3Et3N 1 150 5.52 AGL (30%)/1- 89.03 45.68 BuOH (70%) 4Et3N 3 150 5.52 AGL (30%)/1- 98.88 51.31 BuOH (70%) 5 Dabco 3 150 5.52 AGL (30%)/1- 99.22 58.01 BuOH (70%) 6 20% 3 150 5.52 AGL (30%)/1- 96.97 55.68 CsOAc/KA-160 BuOH (70%) SiO2 7 20% 3 150 5.52 AGL (30%)/1- 98.96 53.36 RbOAc/KA-160 BuOH (70%) SiO2 8 20% 1 150 5.52 AGL (30%)/1- 91.87 37.56 CsOAc/KA-160 BuOH (70%) SiO2 9 20% 1 150 5.52 AGL (30%)/1- 95.42 42.01 RbOAc/KA-160 BuOH (70%) SiO2 10 20% 3 100 5.52 AGL (30%)/1- 62.59 20.94 CsOAc/KA-160 BuOH (70%) SiO2 11 20% 3 100 5.52 AGL (30%)/1- 63.21 21.98 RbOAc/KA-160 BuOH (70%) SiO2 12Li2CO3 3 100 5.52 AGL (30%)/1- 22.52 79.06 BuOH (70%) 13Na2CO3 3 100 5.52 AGL (30%)/1- 71.73 32.81 BuOH (70%) 14K2CO3 3 100 5.52 AGL (30%)/1- 59.17 62.23 BuOH (70%) 15Sc2CO3 3 100 5.52 AGL (30%)/1- 33.81 64.46 BuOH (70%) 16Li2CO3 1 150 5.52 AGL (30%)/1- 62.91 82.62 BuOH (70%) 17Na2CO3 1 150 5.52 AGL (30%)/1- 97.30 68.86 BuOH (70%) 18K2CO3 1 150 5.52 AGL (30%)/1- 97.65 65.32 BuOH (70%) 19Sc2CO3 1 150 5.52 AGL (30%)/1- 79.92 70.51 BuOH (70%)
	lithium carbonate; at 100 - 150℃; under 41404.1 Torr; for 1 - 3h;Product distribution / selectivity;	Example 1 General Procedure for the Reaction of Alcohols and alpha-Angelica Lactone A 2 cc pressure vessel was charged with 700 mg of a solution consisting of alcohol, alpha-angelica lactone and 50 mg of a catalyst. The reactor was pressurized with nitrogen and heated to reactor temperature for a specified period of time. The vessel was then cooled, vented and the products analyzed by gas chromatography on a HP-6890 GC (Agilent Technologies; Palo Alto, Calif.) and HP-5972A GC-MS detector equipped with a 25M×0.25MM ID CP-Wax 58 (FFAP) column. The GC yields were obtained by adding methoxyethyl ether as the internal standard. The examples described below were performed according to a similar procedure under the conditions indicated for each example.; Examples 2-19 Reaction of alpha-Angelica Lactone (AGL) with 1-Butanol (1-BuOH) to Produce Butyl Levulinate (BuLV) N2 AGL BuLV Expt. Time Temp Pressure Conversion Selectivity No. Basic Catalyst (hrs) ( C.) (MPag) Feedstock (%) (%) 2Et3N 3 100 5.52 AGL (30%)/1- 77.56 29.08 BuOH (70%) 3Et3N 1 150 5.52 AGL (30%)/1- 89.03 45.68 BuOH (70%) 4Et3N 3 150 5.52 AGL (30%)/1- 98.88 51.31 BuOH (70%) 5 Dabco 3 150 5.52 AGL (30%)/1- 99.22 58.01 BuOH (70%) 6 20% 3 150 5.52 AGL (30%)/1- 96.97 55.68 CsOAc/KA-160 BuOH (70%) SiO2 7 20% 3 150 5.52 AGL (30%)/1- 98.96 53.36 RbOAc/KA-160 BuOH (70%) SiO2 8 20% 1 150 5.52 AGL (30%)/1- 91.87 37.56 CsOAc/KA-160 BuOH (70%) SiO2 9 20% 1 150 5.52 AGL (30%)/1- 95.42 42.01 RbOAc/KA-160 BuOH (70%) SiO2 10 20% 3 100 5.52 AGL (30%)/1- 62.59 20.94 CsOAc/KA-160 BuOH (70%) SiO2 11 20% 3 100 5.52 AGL (30%)/1- 63.21 21.98 RbOAc/KA-160 BuOH (70%) SiO2 12Li2CO3 3 100 5.52 AGL (30%)/1- 22.52 79.06 BuOH (70%) 13Na2CO3 3 100 5.52 AGL (30%)/1- 71.73 32.81 BuOH (70%) 14K2CO3 3 100 5.52 AGL (30%)/1- 59.17 62.23 BuOH (70%) 15Sc2CO3 3 100 5.52 AGL (30%)/1- 33.81 64.46 BuOH (70%) 16Li2CO3 1 150 5.52 AGL (30%)/1- 62.91 82.62 BuOH (70%) 17Na2CO3 1 150 5.52 AGL (30%)/1- 97.30 68.86 BuOH (70%) 18K2CO3 1 150 5.52 AGL (30%)/1- 97.65 65.32 BuOH (70%) 19Sc2CO3 1 150 5.52 AGL (30%)/1- 79.92 70.51 BuOH (70%)

Reference： [1]ChemCatChem,2017,vol. 9,p. 2747 - 2759
[2]Catalysis science and technology,2020,vol. 10,p. 3255 - 3264
[3]Patent: US2005/210738,2005,A1 .Location in patent: Page/Page column 5
[4]Patent: US2005/210738,2005,A1 .Location in patent: Page/Page column 5-6
[5]Patent: US2005/210738,2005,A1 .Location in patent: Page/Page column 5
[6]Patent: US2005/210738,2005,A1 .Location in patent: Page/Page column 5-6
[7]Patent: US2005/210738,2005,A1 .Location in patent: Page/Page column 5-6
[8]Patent: US2005/210738,2005,A1 .Location in patent: Page/Page column 5
[9]Patent: US2005/210738,2005,A1 .Location in patent: Page/Page column 5-6
[10]Patent: US2005/210738,2005,A1 .Location in patent: Page/Page column 5-6
[11]Patent: WO2005/97723,2005,A2 .Location in patent: Page/Page column 18
[12]Patent: WO2005/97723,2005,A2 .Location in patent: Page/Page column 18
[13]Patent: WO2005/97723,2005,A2 .Location in patent: Page/Page column 18
[14]Catalysis science and technology,2015,vol. 5,p. 5168 - 5173
[15]ChemSusChem,2017,vol. 10,p. 1494 - 1500

21
[ 597-09-1 ]
[ 2052-15-5 ]
[ 145290-18-2 ]
[ 145277-24-3 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In toluene;	EXAMPLE 2 Preparation of 5-Amino-5-ethyl-2-carbobutoxyethyl-2-methyl-1,3-dioxane 7.46 g of 2-nitro-2-ethyl-1,3-propanediol, 8.61 g of <strong>[2052-15-5]butyl levulinate</strong>, 50 mg of p-toluenesulfonic acid in 50 ml of toluene was refluxed until no more water separated. The reaction mixture was cooled, washed with 2% sodium bicarbonate and water, dried and concentrated to give 13.65 g of 2-carbobutoxyethyl-2-methyl-5-nitro-5-ethyl-1,3-dioxane as a light yellow oil. This was dissolved in 50 ml of ethanol and hydrogenated over 1 g Raney Nickel catalyst at 60 under pressure. Distillation of the crude material at 160 C./3mm gave 11 g of the product.

Reference： [1]Patent: US5482965,1996,A

22
None [ No CAS ]
[ 71-36-3 ]
C₁₂H₂₂O₅ [ No CAS ]
C₁₂H₂₂O₅ [ No CAS ]
C₈H₁₃O₅^(1-)*Na⁽¹⁺⁾ [ No CAS ]
[ 2052-15-5 ]
[ 19856-23-6 ]
[ 56-81-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; at 20℃; for 24h;Product distribution / selectivity;	Example 18; 301.2 g of the polymer prepared according to Example 9 were stirred with 500 ml of n-butanol containing 6 grams of sodium hydroxide at room temperature for 24 hours. The resulting transparent yellowish solution was stripped of excess n- butanol on a rotary evaporator under reduced pressure, and the whole was mixed <n="44"/>with 600 ml of n-heptane in a separatory funnel. The lower layer, containing primarily glycerol and sodium levulinate and the sodium salt of the compound of formula (3), wherein R3 is H, was discarded, and the upper layer was filtered through a paper towel. The resulting practically colorless filtrate was stripped of heptane on a rotary evaporator, to yield a clear colorless liquid (385 g) that was analyzed by GC-MS. The liquid was found to contain approximately 24% butyl levulinate and approximately 73% of a 1:1 mixture of cis- and fr-alphaws-isomers of the compound of formula (3), wherein R3 is n-butyl.The compound (3) was then further purified by distilling out butyl levulinate at a reduced pressure.

Reference： [1]Patent: WO2007/62118,2007,A2 .Location in patent: Page/Page column 42-43

23
[ 505-23-7 ]
[ 2052-15-5 ]
[ 1126748-68-2 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 1361 - 1365

24
[ 2052-15-5 ]
[ 56-81-5 ]
C₁₂H₂₂O₅ [ No CAS ]
C₁₂H₂₂O₅ [ No CAS ]
C₁₂H₂₂O₅ [ No CAS ]
C₁₂H₂₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	sulfuric acid; at 110℃; under 25 - 300 Torr; for 0.333333h;Product distribution / selectivity;	Examples 46-47; Using the procedure described in Example 2, 1377.4 g (7.33mol) of <strong>[2052-15-5]butyl levulinate</strong> (obtained from Langfang Triple Well Chemicals Company, Ltd. Of Langfang City, HeBei, China), 245.6g (2.67mol) (E), and 25.38mul (4.8xlO"4 mol) (F) <n="36"/>were reacted. The reaction product was determined by GC-MS to be 61.4% <strong>[2052-15-5]butyl levulinate</strong> and 37.6% of the glycerol ketal of <strong>[2052-15-5]butyl levulinate</strong>. The reaction product had an initial oligomer content of approximately 1.0% according to the total % area of the GC-MS peaks for oligomer products. The reaction product was acidic due to the fact that the sulfuric acid catalyst had not been removed, nor had any other trace acids been removed.A 583.35g aliquot of the reaction product was placed into a 1 liter, 3 -neck roundbottom flask equipped with a thermocouple, a magnetic stirrer, and a distillation column with 3 receiving flasks. All distillable liquids were removed under vacuum of 35 Torr over a temperature range of about 1100C to 21 O C . After the distillation, 133.74g of undistilled bottoms remained in the flask. The oligomer content of the undistilled bottoms was measured by GC and the final oligomer content had risen from 1.0% to 10.2%. The yield of undistilled bottoms was 22.9% of the total weight of the total reaction product prior to distillation. A 930.2g aliquot of the reaction product and 93.0 g of (N) were placed into a2 liter Erlenmeyer flask and stirred for 1 hour. The mixture was filtered to remove the solids and 832.32g of the filtrate was transferred into a 1 liter 3-neck roundbottom flask equipped with a thermocouple, a magnetic stirrer, and a distillation column with 3 receiving flasks. All distillable liquids were removed under vacuum of 35 Torr over a temperature range of about 11O0C to 210 C. After the distillation, 47.06 g of undistilled bottoms remained in the flask. The oligomer content of the distillation bottoms was measured by GC and the final oligomer content had risen from 1.0% to 5.6%. The yield of undistilled bottoms was 5.7% of the total weight of the total reaction product prior to distillation.

Reference： [1]Patent: WO2009/48874,2009,A1 .Location in patent: Page/Page column 34-35

25
[ 1623-88-7 ]
[ 71-36-3 ]
[ 592-84-7 ]
[ 2052-15-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	at 110℃; for 2h;	A mixture of CMF (1, 9.221 g, 63.79 mmol) and n-BuOH (50 mL) was heated at 110 C. for 2 hours. Distillation between 104-110 C. gave a mixture of n-butyl formate (5.649 g, 87%) and recovered n-BuOH (16.40 g). Distillation of the residue at 90-91 C./2 mm gave n-butyl levulinate (9.277 g, 84%).

Reference： [1]Green Chemistry,2010,vol. 12,p. 370 - 373
[2]Patent: US2009/234142,2009,A1 .Location in patent: Page/Page column 8

26
[ 2052-15-5 ]
xylitan [ No CAS ]
C₁₄H₂₄O₆ [ No CAS ]
C₁₄H₂₄O₆ [ No CAS ]
C₁₄H₂₄O₆ [ No CAS ]
C₁₄H₂₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	toluene-4-sulfonic acid; at 21℃; for 24h;Inert atmosphere;	Example 7 cis isomers"BuAXLK" - mixture of stereoisomersA reaction was carried out according to the procedure of Example 6, except that 5.05g (0.03mol) of <strong>[2052-15-5]butyl levulinate</strong> was used instead of ethyl levulinate.After 24 hours, a 99+ % conversion of AXMIBK to BuAXLK was measured using the GC-MS techniques described in Example 6. No crystallization was observed to occur in the reaction mixture. The final product had a 4.02: 1 ratio of translcis isomers.

Reference： [1]Patent: WO2010/138842,2010,A1 .Location in patent: Page/Page column 50-51

27
[ 2052-15-5 ]
[ 491-19-0 ]
[ 1256480-53-1 ]
[ 1256480-53-1 ]

Yield	Reaction Conditions	Operation in experiment
	sulfuric acid; at 90℃; under 9 - 12 Torr; for 0.666667h;	Example 17; A 1 -liter 3-neck round bottom flask was charged with 386 g (2.24mol) n-<strong>[2052-15-5]butyl levulinate</strong>, 15Og (1.12 mol) of 1,4-anhydroxylitol prepared according to the Example 3B, and 5.4 mg (0.055 mmol) of 98% sulfuric acid. The contents of the flask were observed to form two distinct liquid layers. The flask was equipped with an overhead mechanical stirrer, a Dean-Stark separator with an overhead condenser and vacuum/nitrogen inlet, and thermocouple. The contents of the flask were heated to9O0C by means of an oil bath, under reduced pressure of about 9-12 Torr while stirring for approximately 40 minutes, and a liquid was collected in the Dean Stark trap. After collection of liquid subsided, the contents of the flask were allowed to cool to room temperature, and a sample of the crude product was removed for GC-MS analysis. The analysis showed that the crude product was about 42.1% n-<strong>[2052-15-5]butyl levulinate</strong>, about 1.6% 1,4-anhydroxylitol, and about 55.3% 1 ,4-anhydroxylitol levulinate ketal, butyl ester (BuAXLK).The crude product was washed once with an equal volume of a 1 wt % aqueous solution of sodium carbonate and then twice with an equal volume of 0.2 wt % aqueous sodium bicarbonate solution in a separation funnel. A sample of the washed product was removed for GC-MS analysis. The GC trace showed that the unreacted 1,4-anhydroxylitol was completely removed. Residual <strong>[2052-15-5]butyl levulinate</strong> and any traces of water were distilled out under reduced pressure using a rotary evaporator (17O0C, 20 Torr). The resulting liquid was distilled using a rotary evaporator using an oil bath set to 170- 1750C and reduced pressure of 0.2-0.6 Torr. The resulting distilled colorless liquid product (155 g) was analyzed by GC-MS and was found to be over 99% 1,4-anhydroxylitol levulinate ketal, butyl ester (BuAXLK), present as a 3:1 mixture oitrans:cis isomers.

Reference： [1]Patent: WO2010/138842,2010,A1 .Location in patent: Page/Page column 56-57

28
[ 56920-82-2 ]
[ 2052-15-5 ]

Reference： [1]ChemSusChem,2011,vol. 4,p. 112 - 118
[2]ChemSusChem,2014,vol. 7,p. 835 - 840

29
[ 2052-15-5 ]
[ 108-29-2 ]

Yield	Reaction Conditions	Operation in experiment
94.09%	With aluminum isopropoxide; isopropyl alcohol; at 40 - 160℃; for 0.666667h;Microwave irradiation;	To the glass reaction tube was added 0.5 g of <strong>[2052-15-5]butyl levulinate</strong>,8 g isopropyl alcohol,0.25 g of aluminum isopropoxide,Stir evenly,Add stirrups,Installed and placed in the microwave synthesis reactor;Set the initial microwave power of 300W,Set the temperature 160 ,The reaction conditions were maintained for 40 min,The reaction was carried out at constant speed with stirring,After the reaction is over,The system was rapidly cooled to 40 C by air cooling and the reaction mixture was removed.By gas chromatography analysis,The conversion of <strong>[2052-15-5]butyl levulinate</strong> was 100%The yield of GVL was 94.09%.
91.14%	In isopropyl alcohol; at 180℃; for 5h;Autoclave;	General procedure: CTH reaction of ML was performed without stirring in a steel alloy autoclave (Fe-Cr-Ni alloy, GB1220-92) with an internal volume of 35 ML. Typically, carbonyl compounds (0.67 mmol), solvents (20 mL), and catalyst (0.1 g) were charged into the reactor, which was then sealed and heated to a designed temperature (140-220 C) for an intended reaction time (1-24 h). After the reaction, the autoclave was taken out and cooled to ambient temperature. Identification of liquid products in the reaction mixture wasachieved by the TRACE ISQ GC-MS (Thermo Scientific Co,TR-WAX-MS column 30.0m×320 mum×0.25 mum). The temperatureprogram started at 60 C for 1 min, then increased from 60 C to 230 Cat a rate of 15 C /min and held for 2 min. Identification of liquid products in the reaction mixture wasachieved by the TRACE ISQ GC-MS (Thermo Scientific Co,TR-WAX-MS column 30.0m×320 mum×0.25 mum). The temperature program started at 60 C for 1 min, then increased from 60 C to 230 C at a rate of 15 C /min and held for 2 min.
58%Chromat.	With isopropyl alcohol; at 150℃; under 7500.75 Torr; for 2h;Autoclave; Inert atmosphere;	General procedure: Typical procedure of catalytic reaction is as follows: to a stainless autoclave reactor equipped with a pressure gauge were charged levulinate ester (2 mmol), ZrO2 catalyst (40 mg as ZrO2), alcohol (10 mL), and a stirring bar. The reactor was purged and pressurized with 1.0 MPa of Ar. The reaction was performed at 150 C for 2 h with magnetic stirring. After cooling to room temperature, the reaction mixture was filtered and analyzed by FID-GC.

71%Chromat.

With isopropyl alcohol; at 150℃; under 7500.75 Torr; for 3h;Autoclave; Inert atmosphere;

General procedure: In a typical reaction, a reaction mixture containing catalyst(40 mg as ZrO2), substrate (2 mmol), and alcohol (10 mL) wascharged into a 60 mL cylindrical stainless steel high-pressure reac-tor (EYELA, Inc.) equipped with a bourdon pressure gauge, whichwas then sealed, purged and pressurized with 1.0 MPa of Arand then heated to 150C. During the reaction, magnetic stir-ring at 600 rpm was continued. After the predetermined reactiontime, the reactor was cooled to room temperature and the liq-uid products recovered from the reaction mixture were analyzedby a gas chromatograph (Shimadzu GC-14B) with a frame ioniza-tion detector equipped with a capillary column (ULBON HR-20 M;0.53 mm × 30 m; Shinwa Chemical Ind., Ltd.). Conversion of sub-strate and yields of products were quantified using biphenyl as aninternal standard. To assess the catalyst reusability, the spent cat-alyst was retrieved from the reaction mixture by filtration, washedwith acetone, dried at 100C and then subjected to multiple cat-alytic runs (for detailed procedures for catalyst reusability test, seethe Supplementary Information).

Reference： [1]Patent: CN106432144,2017,A .Location in patent: Paragraph 0028; 0029
[2]Molecular catalysis,2017,vol. 442,p. 107 - 114
[3]Molecular catalysis,2019,vol. 467,p. 52 - 60
[4]Chemical Communications,2011,vol. 47,p. 12233 - 12235
[5]Green Chemistry,2012,vol. 14,p. 1260 - 1263
[6]Bulletin of the Chemical Society of Japan,2014,vol. 87,p. 1252 - 1254
[7]Angewandte Chemie - International Edition,2015,vol. 54,p. 9399 - 9403
Angew. Chem.,2015,vol. 127,p. 9531 - 9535,5
[8]Catalysis science and technology,2016,vol. 6,p. 5374 - 5379
[9]Catalysis Today,2017,vol. 281,p. 418 - 428
[10]ChemCatChem,2016,vol. 8,p. 3769 - 3779
[11]Molecular catalysis,2017,vol. 442,p. 181 - 190
[12]RSC Advances,2014,vol. 4,p. 45848 - 45855
[13]ChemCatChem,2018,vol. 10,p. 222 - 233

30
agar [ No CAS ]
[ 71-36-3 ]
[ 1917-68-6 ]
[ 2052-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	Dowex 50WX8-200 ion exchange resin; at 90℃; for 3h;Product distribution / selectivity;	Exemplary Embodiment 4-2Production of 5-butoxymethyl-2-furfural and Levulinic Acid Butyl Ester, with 5% Agar Solution1 g of agar, 1 g of Dowex ion exchange resin as a solid acid catalyst, and 20 mL of n-butanol as a solvent and a reagent were put into a 250 mL round bottom flask and stirred to make suspension. Further, a reflux condenser was installed and temperature was slowly raised up to 90 C. Then, the suspension was stirred at 240 rpm, and reacted for 30 hours. At this time, colorless solution was changed to be brown (when about 4 to 5 hours elapse after the reaction initiation). After the reaction, a solid acid catalyst and a solid material based on a side reaction in a reaction mixture, i.e., humin ware filtered off, and a mixture produced by removing the solvent of the remaining solution under decompression was separated by the column chromatography (hexane:ethyl acetate=10:1?5:1) to thereby produce a mixture of 5-butoxymethyl-2-furfural and levulinic acid butyl ester at a yield of 20% (200 mg).

Reference： [1]Patent: US2012/53355,2012,A1 .Location in patent: Page/Page column 9

31
[ 2052-15-5 ]
[ 129549-67-3 ]
[ 108-29-2 ]
[ 71-36-3 ]

Reference： [1]ChemSusChem,2011,vol. 4,p. 1838 - 1843

32
[ 9004-34-6 ]
[ 71-36-3 ]
[ 64-18-6 ]
[ 592-84-7 ]
[ 2052-15-5 ]
[ 123-76-2 ]

Reference： [1]ChemSusChem,2011,vol. 4,p. 1838 - 1843

33
[ 79-24-3 ]
[ 141-32-2 ]
[ 2052-15-5 ]
[ 106251-92-7 ]

Yield	Reaction Conditions	Operation in experiment
		To DCM solution (10 mL) of nitro methane/nitro ethane (1 eq.) was added Cs2CO3 (1 eq.) and the contents stirred for five minutes, followed by the addition of a mixture of appropriate acrylate (1 eq., in 3 mL DCM) and catalytic amount of CuCN (pinch) and the reaction mixture stirred at 30-32 ºC. The progress of reaction was monitored by TLC. On completion of reaction, the contents were diluted with water, the organic layer separated and the aqueous portion extracted with DCM (3x 50 mL). The combined organic layer washed with water (2x10 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure at <40 oC. The crude reaction product was purified by column chromatography over silica gel (mesh 60-120) using hexane and ethyl acetate (19:1) as eluent to obtain nitro and keto diester products.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 3305 - 3309

34
[ 470-23-5 ]
[ 71-36-3 ]
[ 1917-68-6 ]
[ 2052-15-5 ]