Acetic Acid → Benzamide

HRID 1731065Notes

Reaction equation

HRID 1731065 reaction equation
C(O)(=[O:3])C.[C:5](#[N:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O.[Zn]>[C:5]([NH2:12])(=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 7505Benzonitrile2×

Product 1

HCID 2331BenzamideYield 24%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

Watanabe, in Bull. Chem. Soc. Japan, 37, 1325 (1964), teaches the conversion of benzonitrile to benzamide with precipitated copper and Urushibara copper (U-Cu). The precipitated copper was prepared from a cupric chloride solution and zinc dust and was reacted with benzonitrile in water for 8 hours to give a 7% yield of benzamide. U-Cu-A was prepared by mixing zinc dust with a solution of cupric chloride and then leaching the resultant product with 13% acetic acid. The reaction of benzonitrile in water with U-Cu-A for 8 hours gave a 24% yield of benzamide with no recovery of benzonitrile.

Sources & evidence

ORD record
ord-54e03adb35fd4370ae8830ee82dac7bd
Source dataset
uspto-grants-1976_11
Patent number
US03994973

Reaction notes

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