Methanol → Methyl 3-hydroxy-4-methoxybenzoate

A mixture of 3-hydroxy-4-methoxybenzoic acid (Aldrich, 10 g, 59.5 mmol), methanol (250 ml) and concentrated sulfic acid (1 ml) was stirred overnight and the product was poured into a mixture of sodium bicarbonate and ice. The aqueous mixture was then extracted three times with ethyl acetate. The resulting organic layers were combined, washed with water and brine, and dried over anhydrous magnesium sulfate. Rotary evaporation of the solution gave 9.5 g of the desired product as a colorless oil. NMR (δ):3.89 (s, 3H), 3.95 (s, 3H).

1. concentrationconcentrated sulfic acid (1 ml)
2. additionthe product was poured into a mixture of sodium bicarbonate and ice
3. extractionThe aqueous mixture was then extracted three times with ethyl acetate
4. washwashed with water and brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customRotary evaporation of the solution

ORD record

ord-922f863457fd4fb68701cc44701971a0

Source dataset

uspto-grants-1998_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05780249