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
- 80 °C
Procedure
A mixture containing ethyl p-cyanobenzoate (87.5 g, 0.5 mol), methanol (192.5 g), water (449.2 g) was placed in a 1 l-flask. The mixture was heated to 80° C. with stirring. 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. Eighteen hours after the reaction started, liquid chromatographic analysis revealed that the reaction mixture contained 64.7 g of p-cyanobenzoic acid (yield 88%). 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., and methanol was added thereto until the mixture dissolves. The resultant mixture was cooled for crystallization, to thereby obtain 64.6 g of p-cyanobenzoic acid crystal (purity 96.7%, yield 85%).
Workup
- customEighteen hours
Sources & evidence
- ORD record
- ord-7e3ff9a70cfe4fdc8132b61097c8596d
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06433211B1
Reaction notes
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