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

HRID 1248469Notes

Reaction equation

HRID 1248469 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

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.

Workup

  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.)

Sources & evidence

ORD record
ord-fef0c1c04bb04a6c8b1f27cbeb97caab
Source dataset
uspto-grants-1985_06
Patent number
US04524206

Reaction notes

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