Water → HCID 178524381, compound

Participants

Reaction Steps

To a solution of methyl 3-[(trans-4-hydroxycyclohexyl)amino]benzoate (0.25 g, 1.00 mmol) in a mixture of methanol (20 mL), terahydrofuran (10 mL) and water (10 mL) was added a 4M aqueous solution of potassium hydroxide (0.5 mL, 2.00 mmol), and the reaction mixture was heated to reflux for five minutes. The organic portion of the solvent was evaporated, and the pH of the aqueous solution was adjusted to 2 by the addition of 2M aqueous hydrochloric acid. The aqueous mixture was partitioned with ethyl acetate, the organic layer was separated and washed with brine, dried over sodium sulfate, filtered, and the solution was concentrated to give 3-[(trans-4-hydroxycyclohexyl)amino]benzoic acid (40 mg, 17%). MS (EI) for C13H17NO3: 234 (M−H).

Provenance & Evidence