p-Cyanobenzamide → Ethyl 4-cyanobenzoate

HRID 2304087Notes

Reaction equation

HRID 2304087 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](N)=[O:8])=[CH:5][CH:4]=1)#[N:2].Cl.[CH2:13]([OH:15])[CH3:14]>C(O)C>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:15][CH2:13][CH3:14])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 76427p-CyanobenzamideHCID 21887872Ethanol hydrochloride

Product 1

HCID 81589Ethyl 4-cyanobenzoateYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-Cyanobenzamide (73.0 g, 0.5 mol) which has a purity of 99% or more and ethanol (460.3 g) were placed in a 2 l-separable flask, and the mixture was allowed to react at 78° C. for 12 hours while a 20% hydrochloric acid/ethanol solution (162.4 g) prepared in advance was added thereto with stirring. Gas chromatographic analysis revealed that the reaction mixture contained 83.1 g of ethyl p-cyanobenzoate (yield 95%). Subsequently, the reaction mixture was concentrated under reduced pressure, and water was added thereto. The resultant mixture was dissolved through heating, and cooled for crystallization, to thereby obtain 74.7 g of ethyl p-cyanobenzoate having a purity of 99.5% (yield 85%).

Workup

  1. customprepared in advance
  2. additionwas added

Sources & evidence

ORD record
ord-d9144d7bb4ce46ebbc40b22f500ca473
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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