Potassium Hydroxide → 1,4-Benzodioxane-6-carboxylic Acid

Participants

Reaction Steps

2,3-Dihydro-benzo[1,4]dioxine-6-carboxaldehyde (2.03 g, 12.4 mmol), was slurried in water (50 ml) at 80° C. Potassium permanganate (2.70 g, 17.1 mmol) as a solution in water (50 ml) was added over 1 hour. The mixture was then heated for a further 2 hours after which time the reaction mixture was basified with 10% aqueous potassium hydroxide. The resulting precipitate was removed by filtration and washed with water (2×50 ml). The combined filtrates were acidified with concentrated hydrochloric acid and the resulting solid isolated by filtration and dried under vacuum. This provided the desired compound as a white solid (1.50 g, 67%).

Provenance & Evidence