Sodium Chloride → Hydrochloric Acid

Participants

Reaction Conditions

Reaction Steps

To a solution of the sodium chloride salt of 3-isopropenyl-5-(5-methylpyridin-2-yl)benzoic acid (2.114 g, 4.93 mmol) in water (49.3 mL) at 0° C. was added methanesulfonic acid (23.7 mL, 247 mmol) and the mixture was heated to 50° C. After 16 h, the mixture was cooled to 0° C. and sodium hydroxide (9.86 g, 247 mmol) added. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. The mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→65% water/acetonitrile with 0.1% trifluoroacetic acid). Treatment with 2 M hydrochloric acid in diethyl ether gave the title compound as a hydrochloride salt (1.252 g). MS 272.0 (M+1).

Provenance & Evidence