Methanol → Methyl 3-tert-butyl-4-hydroxybenzoate

Participants

Reaction Conditions

Reaction Steps

Methyl 4-hydroxybenzoate (3.00 g) was dissolved in methanesulfonic acid (15 mL), and 2-bromo-2-methylpropane (11.1 mL) was added to the solution, and then the mixture was stirred at 70° C. for 16 hours. To the reaction solution, methanol (20 mL) was added, and then the reaction mixture was stirred at 50° C. for 3 hours. 1N potassium hydroxide was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous 10% potassium carbonate solution and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (1.83 g) as a pale yellow crystal.

Provenance & Evidence