Hydrochloric Acid → 4-Hydroxy-2-methoxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of the methyl 2-methoxy-4-hydroxybenzoate (27 g, 147 mmol) from Step 3 above in MeOH (250 mL) was added 2N sodium hydroxide (147 mL, 2 eq) and the reaction was stirred for 5 hours at 40° C. The reaction was brought to pH 4 with the addition of 6N HCl and the solvent was reduced to one-third volume under reduced pressure. The aqueous mixture was extracted with methylene chloride (5×300 mL) and the combined organic phases were washed with water, brine, and dried over MgSO4. The solution was filtered and the solvent removed under reduced pressure to give a solid which was suspended in ether and filtered. 2-Methoxy-4-hydroxybenzoic acid was obtained in 80% yield.

Provenance & Evidence