Methanol → 3-Cyanobenzoic acid
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]CC)=[O:7])#[N:2].CO.[OH-].[Na+]>O>[C:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[C:6]([OH:8])=[O:7])#[N:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 82 °C
Procedure
A mixture containing ethyl m-cyanobenzoate (87.5 g, 0.5 mol), methanol (192.5 g), and water (449.2 g) was placed in a 1 l-flask, and heated to 82° C. with stirring by use of a mechanical stirrer. When the temperature became stable, a 20% aqueous solution of sodium hydroxide was added thereto so as to adjust the pH of the mixture at 9.0-9.3. Four hours after the reaction started, 20% sodium hydroxide (98.2 g) was added to the mixture. Liquid chromatographic analysis revealed that the reaction mixture contained 68.4 g of m-cyanobenzoic acid (yield 93%). The reaction mixture was cooled to 30° C., and hydrochloric acid was added thereto to lower the pH of the mixture to 3.1. The mixture was heated again to 82° C., and methanol was added thereto until the mixture dissolves. The mixture was cooled so as to crystallize, to thereby obtain 63.8 g of m-cyanobenzoic acid crystal (purity 96.8%, yield 84%).
Workup
- customFour hours
Sources & evidence
- ORD record
- ord-816f1441b98a4543808aeb5f6c14928e
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06433211B1
Reaction notes
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