Methanol → 3-(1-(Dimethylamino)-2-methylpentan-3-yl)phenol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of [1RS,2RS]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenyl ester (9 g, 0.02 mol) and methanol (27 ml), a solution of sodium hydroxide (4 g, 0.10 mol) and water (18 ml) was added at 20-25° C. and mixture was stirred at 28-35° C. for 20 hours. Reaction mixture was further stirred at 45-50° C. for 6 hours and solvent was distilled off. Resulting residue was dissolved in demineralised water (30 ml) at ambient temperature and washed with isopropyl ether (2×10 ml). Aqueous layer was separated and aqueous hydrochloric acid (7.3 ml, 30%) was added at 20-25° C. reaction mixture was saturated with sodium chloride and extracted with ethyl acetate (2×50 ml). All ethyl acetate extracts were combined, washed with water, dried and solvent was distilled off to give 4.24 g of title compound.

Provenance & Evidence