Methanol → Methyl 3,5-Dihydroxybenzoate

To a solution of 3,5-dihydroxybenzoic acid (50.0 g, 320 mmol) in methanol (310 ml) was added concentrated sulfuric acid (7.7 ml) and the resultant solution heated at reflux for 16 hrs. It was then cooled and approximately 200 ml of methanol removed under reduced pressure. To the remaining solution was added water (300 ml) and the mixture extracted with ether (4×50 ml). The combined extracts were washed with saturated aqueous sodium bicarbonate (50 ml), dried, and evaporated to dryness. The resultant solid was recrystallized from 50 ml of methanol/125 ml of water to give methyl 3,5-dihydroxybenzoate as off-white crystals (50.1 g, 91.9%).

1. temperatureat reflux for 16 hrs
2. temperatureIt was then cooled
3. customapproximately 200 ml of methanol removed under reduced pressure
4. additionTo the remaining solution was added water (300 ml)
5. extractionthe mixture extracted with ether (4×50 ml)
6. washThe combined extracts were washed with saturated aqueous sodium bicarbonate (50 ml)
7. customdried
8. customevaporated to dryness
9. customThe resultant solid was recrystallized from 50 ml of methanol/125 ml of water

ORD record

ord-7b3ff72e9da44e9d8feaef8bff97cb9c

Source dataset

uspto-grants-1991_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05041516