1,3-Dimethoxy-2-propylbenzene → 1,3-Benzenediol, propyl-

Participants

Reaction Conditions

Reaction Steps

A mixture of solid 1,3-dimethoxy-2-propylbenzene (33.70 g, 190 mmoles) and solid pyridine hydrochloride (150 g, 1.30 mole) was warmed to 180° C. After 7.5 hours the reaction was cooled to 110° C. and 50 ml of water was added slowly. After the reaction cooled to room temperature, it was diluted with 100 ml of water and extracted several times with ethyl acetate. The ethyl acetate extract was washed once with 2N hydrochloric acid and then dried over magnesium sulfate. Filtration and solvent removal gave 38.5 g of an orange solid. The title product was purified by recrystallization from dichloromethane providing 11.86 g (41%) of yellow crystals.

Provenance & Evidence