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

HRID 910179ノート

反応式

HRID 910179 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 29024Ethyl 2-cyano-3-phenyl-2-butenoate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

A stirred mixture of acetophenone (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 (MgSO4) 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 which was used without further purification.

後処理

  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 (MgSO4)
  6. customthe solvent was removed in vacuo
  7. distillationThe residual oil was distilled under reduced pressure

出典と根拠

ORDレコード
ord-a0d70390de0240cf887f730f6bb0920b
出典データセット
uspto-grants-2011_09
特許番号
US08022076B2

反応ノート

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