Ethanol → Ethyl 3-cyano-3-phenylpropanoate

HRID 1076882Notes

Reaction equation

HRID 1076882 reaction equation
C(OC(=O)[C:5](=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[C-:19]#[N:20].[K+].C(O)C>O>[CH2:9]([O:8][C:6](=[O:7])[CH2:5][CH:11]([C:19]#[N:20])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH3:10]

Participants

5

Reactant 3

HCID 702EthanolHCID 9032Potassium CyanideHCID 94751Diethyl (phenylmethylene)malonate

Product 1

HCID 12414061Ethyl 3-cyano-3-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

120 g of benzalmalonic acid diethyl ester, 33.6 g of potassium cyanide, 1600 cc of ethanol and 160 cc of water are stirred at a bath temperature of 60° for 12 to 14 hours. The reaction mixture is then cooled with ice water, the potassium bicarbonate which crystallizes is filtered off, the filtrate is made neutral with about 15 cc of 1 N hydrochloric acid, air is passed through the solution with a water jet vacuum pump for 1 hour, the solvent is distilled off on a rotary evaporator, 100 cc of water are added to the oily residue, and extraction is effected 6 times with 250 cc amounts of ether. The 3-cyano-3-phenyl-propionic acid ethyl ester, obtained after distilling off the ether, is purified by vacuum distillation. B.P. 125°-130°/0.15 mm Hg.

Workup

  1. customthe potassium bicarbonate which crystallizes
  2. filtrationis filtered off
  3. distillationthe solvent is distilled off on a rotary evaporator, 100 cc of water
  4. additionare added to the oily residue, and extraction

Sources & evidence

ORD record
ord-d6029a477334409b996241ed14078935
Source dataset
uspto-grants-1976_05
Patent number
US03958003

Reaction notes

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