Sulfuric Acid → 4-Cyanobenzoic acid
Reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](N)=[O:8])=[CH:5][CH:4]=1)#[N:2].Cl[O-].[Na+].S(=O)(=O)(O)[OH:16]>O>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:16])=[O:8])=[CH:5][CH:4]=1)#[N:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
Procedure
p-Cyanobenzamide (146 g) which had been synthesized separately and water (584 g) were placed in a four-neck flask, and the mixture was cooled to 15° C. with stirring. Subsequently, an aqueous solution (1775 g) of sodium hypochlorite (effective chlorine 12%) was added to the reaction mixture over six hours while a 50% aqueous solution of sulfuric acid was added so as to maintain the pH of the mixture at 5-6. Liquid chromatographic analysis revealed that the reaction mixture contained 145.5 g of crude p-cyanobenzoic acid (yield 99%). To the reaction mixture, concentrated sulfuric acid was added so as to adjust the pH to 3.0 and precipitate p-cyanobenzoic acid from its salt. The precipitate was dissolved by adding methanol (820 g) with heat, and the solution was cooled for crystallization, to thereby obtain 138.9 g of p-cyanobenzoic acid having a purity of 99.5% (yield 94%).
Workup
- additionwas added so as
- temperatureto maintain the pH of the mixture at 5-6
Sources & evidence
- ORD record
- ord-9a3ad1d8faab46e784d48b305359e50e
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06433211B1
Reaction notes
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