Abstract Metal-ammonia reduction followed by in situ alkylation of 2-methoxybenzoic acids often results in substantial loss of the methoxy substituent; reduction of the carboxylate salts or esters, however, suppresses this side reaction and good to excellent yields of desired products are then obtained.
[Schultz, Arthur G.; Dittami, James P.; Lavieri, Frank P.; Salowey, Christina; Sundararaman, Padmanabhan; Szymula, Mary Beth Journal of Organic Chemistry, 1984 , vol. 49, # 23 p. 4429 - 4440]
