Ethanol → 4-Cyanobenzoic acid

HRID 2304104Notes

Reaction equation

HRID 2304104 reaction equation
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9]CC)=[O:8])=[CH:5][CH:4]=1)#[N:2].C(O)C.[OH-].[Na+]>O>[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 81589Ethyl 4-cyanobenzoate

Product 1

HCID 120874-Cyanobenzoic acidYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture containing ethyl p-cyanobenzoate (87.5 g, 0.5 mol), ethanol (192.5 g), and water (449.2 g) was placed in a 1 l-flask. The mixture was heated to 60° C., and a 20% aqueous solution of sodium hydroxide was added thereto so as to adjust the pH of the mixture at 9.9-10.0. Twenty-three hours after the reaction started, liquid chromatographic analysis revealed that the reaction mixture contained 60.3 g of p-cyanobenzoic acid (yield 82%).

Workup

  1. customTwenty-three hours

Sources & evidence

ORD record
ord-3ad42755ba56457394a45d46ab0a062d
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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