Hydrochloric Acid → Methyl 6-hydroxy-2-naphthoate

Participants

Reaction Steps

Treat a mixture of 6-hydroxy-2-naphthoic acid (4.45 g, 23.6 mmol) in 2,2-dimethoxypropane (235 mL) with conc. HCl (24 mL) and then MeOH (60 mL). Stir the reaction at RT for 16 h and then at 55° C. for 16 h. Pour the reaction mixture into EtOAc (250 mL) and wash with brine (3×100 mL). Dry the organic layer over Na2SO4, concentrate the filtrate, and chromatograph the concentrated filtrate (0.5 kg silica gel, 5:95 to 15:85 EtOAc:hex) to give the title compound (4.77 g, quant). MS (ES) m/e 203 (M+1).

Provenance & Evidence