Hydrochloric Acid → 3-Benzyloxy-p-anisic acid

Participants

Reaction Steps

A solution of potassium permanganate (24.81 g, 0.157 moles) in water (0.1 l) was added under stirring with a solution of tetrabutylammonium bromide (50.61 g, 0.157 moles) in water (0.2 l). The formed solid was separated by filtration, washed with water, squeezed, then dissolved in pyridine (0.3 l). The solution was dropped into a solution of 3-benzyloxy-4-methoxy benzaldehyde (38.2 g, 0.157 moles) in pyridine (0.15 l) in water bath. After 3 hours the reaction mixture was brought to acidic pH by 1N HCl, the solid was filtered off and the mother liquor extracted more times in methylene chloride. The organic phases were anhydrified and concentrated to dryness and the residue taken up with 1N NaOH and washed with ethyl ether. The aqueous solution was acidified and extracted twice with methylene chloride, brought to dryness, discoloured with TONSIL® and concentrated to small volume. The resulting precipitate was filtered to give 35.869 g of the title product (yield: 88%)

Provenance & Evidence