Water → 3-Hydroxy-2-methylbenzoic Acid

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Reaction Steps

The cycloadduct (1.05 g) from Example 2, 1.80 g of potassium tert-butoxide and 9 mL of tert-butanol were combined and refluxed a total of 9 hours. The reaction mixture was poured into water. Toluene was added. The toluene phase was washed twice with dilute sodium hydroxide solution. The combined aqueous phases were acidified with HCl, then extracted several times with t-butyl acetate. The n-butyl acetate was stripped, and the product dried in a vacuum oven to give 0.87 g of 3-hydroxy-2-methylbenzoic acid, 94% purity, 79% yield.

Provenance & Evidence