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

HRID 1248469노트

반응식

HRID 1248469 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1C=CC=CC=1.O>[C:11]([C:13](=[C:8]([CH3:9])[C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 98284'-FluoroacetophenoneHCID 517165Ammonium Acetate

생성물 1

HCID 29024Ethyl 2-cyano-3-phenyl-2-butenoate수율 69.9%

시약·촉매·용매 2

HCID 241Benzene용매2회HCID 962Water용매

실험 절차

A mixture of p-fluoroacetophenone (100 g, 0.72 mole), ethyl cyanoacetate (81.8 g, 0.72 mole), ammonium acetate (13 g, 0.17 mole) and acetic acid (34.7 g, 0.57 mole) is refluxed for 24 hours in benzene (200 mL) with a continuous removal of water by a Dean Stark trap. The cooled mixture is diluted with benzene (150 mL) and extracted with water (2×300 mL). The organic phase is separated, dried (Na2SO4), filtered and concentrated in vacuo to a brown oil. Kugelrohr distillation (125°-127°/0.03 Torr.) affords 108.4 g (64.3%) of product as a yellow green oil.

후처리

  1. extractionextracted with water (2×300 mL)
  2. customThe organic phase is separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a brown oil
  6. distillationKugelrohr distillation (125°-127°/0.03 Torr.)

출처 및 근거

ORD 기록
ord-fef0c1c04bb04a6c8b1f27cbeb97caab
출처 데이터셋
uspto-grants-1985_06
특허 번호
US04524206

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