Dimethylamine → 2-Naphthol, 6-bromo-1-methyl-

Participants

Reaction Steps

Preparation of 6-bromo-1-chloro-2-naphthol 4 from the corresponding 6-bromo-2-naphthol 4a is described in the literature (Buu-Hoi, JOC 1951, 16, 185). 6-Bromo-1-methyl-2-naphthol 7 was prepared as depicted in reaction Scheme I. Reaction of 6-bromo-2-naphthol 4a with aqueous dimethyl amine and aqueous formaldehyde in alcohol afforded the Mannich product 5. Reaction of 5 with acetyl chloride in methylene chloride or chloroform afforded the acetate 6. Hydride reduction of 6 in a solvent such as ethanol followed by basic work-up yielded the desired 6-bromo-1-methyl-2-naphthol 7.

Provenance & Evidence