Hydrochloric Acid → Methyl 3-hydroxy-5-methoxybenzoate

To a solution of methyl 3,5-dihydroxybenzoate (28.0 g) in DMF (300 mL) was added 60% sodium hydride (4.70 g) at 0° C., and the mixture was stirred for 30 min. Iodomethane (23.7 g) was added dropwise, and the mixture was stirred at 0° C. for 1 hr. 1N Hydrochloric acid (300 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (10.1 g) as a white solid.

1. stirringthe mixture was stirred at 0° C. for 1 hr
2. extractionthe mixture was extracted with ethyl acetate
3. washThe extract was washed with saturated brine
4. dry with materialdried over anhydrous sodium sulfate
5. customThe solvent was evaporated under reduced pressure
6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-f67035f5f5af4422a3910f52642d7afc

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181186B2