Water → 4-Cyanobenzoic acid

HRID 2304099Notes

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].O.[OH-].[Na+]>CO>[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

Conditions

Temperature: 80 °C

Procedure

A mixture containing ethyl p-cyanobenzoate (87.5 g, 0.5 mol), water (320.8 g), and methanol (320.8 g) was placed in a 1 l-flask. The mixture was heated to 80° C. with stirring by use of a mechanical stirrer. A 20% aqueous solution of sodium hydroxide was added to the mixture so as to adjust the pH of the mixture at 8.0-8.3. Twenty-four hours after the reaction started, liquid chromatographic analysis revealed that the reaction mixture contained 58.9 g of p-cyanobenzoic acid (yield 80.2%). The reaction mixture was cooled to 30° C., and hydrochloric acid was added thereto to lower the pH to 3.1. The mixture was heated again to 82° C. to dissolve. The resultant mixture was cooled for crystallization, to thereby obtain 57.7 g of p-cyanobenzoic acid crystal (purity 96.8%, yield 76%).

Workup

customTwenty-four hours

Sources & evidence

ORD record: ord-d9c442f99d8d45b9a471fac9d07f1a91
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06433211B1

Reaction notes

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