Hydrochloric Acid → 4-Hydroxy-4′-methoxy[1,1′-biphenyl]-3-carboxylic acid

Participants

Reaction Steps

Palladium(II)acetate (55 mg; 0.23 mmol) was added under argon to a mixture of 5-bromosalicylic acid (5.4 g; 22.4 mmol), sodium carbonate (7.2 g; 68.1 mmol) and 4-methoxyboronic acid (3.8 g; 25 mmol) in water (125 ml). The reaction mixture was stirred at room temperature for 1 h. The resulting slurry was dissolved in hot water (1300 ml) and filtered to give a filtrate and a precipitate. The filtrate was acidified with hydrochloric acid. The precipitate was washed with water and dried in vacuo to give 5.3 g (95%) of 4-hydroxy-4′-methoxy-3-biphenylcarboxylic acid.

Provenance & Evidence