Acetic Acid → Ethyl 2-cyano-3-phenyl-2-butenoate

HRID 1771929노트

반응식

HRID 1771929 반응식
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11].C([O-])(=O)C.[NH4+].C(O)(=O)C>O.C1(C)C=CC=CC=1>[CH2:16]([O:15][C:13](=[O:14])[C:12]([C:10]#[N:11])=[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2])[CH3:17]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 7410AcetophenoneHCID 7764Ethyl cyanoacetateHCID 517165Ammonium Acetate

생성물 1

HCID 29024Ethyl 2-cyano-3-phenyl-2-butenoate수율 110.4%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

A stirred mixture of acetophenone (VIII) (180 g, 1.5 mol), ethyl cyanoacetate (170 g, 1.3 mol), ammonium acetate (23.1 g), acetic acid (72 g) and toluene (300 ml) was heated under reflux for 18 hours while water was removed from the reaction by azeotropic distillation. The mixture was allowed to cool to ambient temperature, toluene (100 ml) was added, then the mixture was washed with water (3×100 ml). The combined aqueous washings were shaken with toluene (50 ml), then the combined toluene solutions were dried over magnesium sulphate, filtered and the solvent was removed in vacuo. The residual oil was distilled under reduced pressure to give 2-cyano-3-phenyl-but-2-enoic acid ethyl ester as an oil (309 g) which was used without further purification.

후처리

  1. temperaturewas heated
  2. customwas removed from the reaction by azeotropic distillation
  3. additiontoluene (100 ml) was added
  4. washthe mixture was washed with water (3×100 ml)
  5. dry with materialthe combined toluene solutions were dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. distillationThe residual oil was distilled under reduced pressure

출처 및 근거

ORD 기록
ord-3ca18dbde67c4f28aa25f7b4bfe3b139
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249155B2

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