Ethyl 3-phenylpropionate → 2-Oxo-4-phenylbutyric acid

HRID 621174

반응식

HRID 621174 반응식
[C:1]1([CH2:7][CH2:8][C:9]([O:11]CC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OCC)(=O)[C:15]([O-:17])=[O:16].[O-]CC.[Na+]>C(O)C>[O:11]=[C:9]([CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:15]([OH:17])=[O:16]

참가 물질

5

반응물 3

HCID 16237Ethyl 3-phenylpropionateHCID 2723922Sodium ethoxideHCID 21943339Ethanedioic acid, monoethyl ester

생성물 1

HCID 697322-Oxo-4-phenylbutyric acid수율 90.9%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 143 g of ethyl 3-phenylpropionate, 234 g of ethyl oxalate and 154 ml of 28% sodium ethoxide solution in ethanol is heated on a water bath at a bath temperature of 60°-70° C. for 1.5 hours, while distilling off the ethanol under reduced pressure. To the resulting red syrupy residue is added 1.3 liters of 15 v/v % sulfuric acid. The mixture is boiled under reflux with stirring for 15 hours, and the oil layer is separated, neutralized with 10% sodium hydroxide and extracted with ethyl acetate. The aqueous layer is made acidic with diluted sulfuric acid. The resulting oil is extracted with ethyl acetate, washed with water and dried. Removal of the ethyl acetate by distillation under reduced pressure gives 130 g of 2-oxo-4-phenylbutyric acid as an oil.

후처리

  1. temperatureis heated on a water bath at a bath temperature of 60°-70° C. for 1.5 hours
  2. distillationwhile distilling off the ethanol under reduced pressure
  3. additionTo the resulting red syrupy residue is added 1.3 liters of 15 v/v % sulfuric acid
  4. temperatureunder reflux
  5. customthe oil layer is separated
  6. extractionextracted with ethyl acetate
  7. extractionThe resulting oil is extracted with ethyl acetate
  8. washwashed with water
  9. customdried
  10. customRemoval of the ethyl acetate
  11. distillationby distillation under reduced pressure

출처 및 근거

ORD 기록
ord-4c287e50f7794ffc9fd27d579d7ed34c
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04822818

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