3-Butenoic acid, 2-oxo-, methyl ester synthesis

4synthesis methods

Product Name:3-Butenoic acid, 2-oxo-, methyl ester
CAS Number:108736-44-3
Molecular formula:C5H6O3
Molecular Weight:114.1

DL-2-HYDROXY-3-BUTENOIC ACID METHYL ESTER

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Yield:108736-44-3 94.4%

Reaction Conditions:

with tris(triphenylphosphine)ruthenium(II) chloride;tert-amyl hydroperoxide in toluene at 0 - 23; for 2 h;Inert atmosphere;

Steps:

2 example 2: Synthesis of methyl 2-oxo-3-butenoate

Add 3 g (24.0 mmol) of acrylonitrile acetate to a 250 mL three-necked flask, add 100 mL of saturated hydrogen chloride methanol solution, stir to dissolve, heat and reflux at 75 ° C for 2 hours, transfer to a single-mouth bottle, and remove hydrogen chloride by rotary distillation. Methanol gives the compound methyl 2-hydroxy-3-butenoate;Methyl 2-hydroxy-3-butenoate was dissolved in 50 mL of toluene and transferred to a three-neck bottle.0.11 g (0.12 mmol) of tris(triphenylphosphine) ruthenium dichloride was added under nitrogen.The system was cooled to 0 ° C, and the tetraamyl hydrogen peroxide was added dropwise with a constant pressure dropping funnel.6.24g (48mmol, 80% content) of 50mL in toluene solution,The drip acceleration maintains the internal temperature of the reaction not exceeding 23 ° C.After about 1 hour, the addition was completed, and after the completion of the dropwise addition, the internal temperature was maintained at 23 ° C for 1 hour.Excessive p-pentyl hydroperoxide was quenched by adding 3 g (24 mmol) of sodium sulfite, stirred for 10 min, filtered, and the filtrate was steamed at not more than 30 ° C and a vacuum of 3.9 KPa to obtain methyl 2-oxo-3-butenoate. The ester was 2.9 g, the GC purity was 96.5%, and the yield was 94.4%.

References:

CN109912416,2019,A Location in patent:Paragraph 0052; 0053

553-90-2 Synthesis