Methanol → 4-Cyanobenzoic acid
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].CO.[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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 82 °C
Procedure
A mixture containing ethyl p-cyanobenzoate (87.5 g, 0.5 mol), methanol (192.5 g), and water (449.2 g) was placed in a 1 l-flask. The mixture was heated to 82° C. with stirring by use of a mechanical stirrer. After the temperature became stable, a 20% aqueous solution of sodium hydroxide was added to the mixture so as to adjust the pH of the mixture at 9.0-9.3. When four hours had elapsed after the reaction started, 20% sodium hydroxide (96.7 g) was added. Liquid chromatographic analysis revealed that the reaction mixture contained 69.1 g of p-cyanobenzoic acid (yield 94%). The reaction mixture was cooled to 30° C., and hydrochloric acid was added to the mixture to lower the pH to 3.1. The mixture was heated again to 82° C., and methanol was added thereto until the mixture dissolved. The resultant mixture was cooled for crystallization, to thereby obtain 64.8 g of p-cyanobenzoic acid crystal (purity 97.5%, yield 86%).
Workup
- customWhen four hours
Sources & evidence
- ORD record
- ord-d6fc784f53af4fa69fc2dbbc32e5b5de
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06433211B1
Reaction notes
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