2,3-Dihydroxybenzoic Acid → Methyl 2,3-Dihydroxybenzoate

To a solution of 2,3-dihydroxybenzoic acid (33.0 g, 214 mmol) in methanol (200 mL) was added sulfuric acid (5.0 mL) and the mixture was refluxed for 14 hours. The solvent was then distilled off under reduced pressure. To that residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure to provide 35.0 g of methyl 2,3-dihydroxybenzoate. A mixture of this compound (35.0 g, 208 mmol), ethyl bromoacetate (70.0 g, 420 mmol), and potassium carbonate (58.0 g, 420 mmol) in acetone (400 mL) was stirred for 14 hours, and filtered. The filtrate was concentrated under reduced pressure to provide 58.0 g of the title compound. Yield 80%. Oil.

1. temperaturethe mixture was refluxed for 14 hours
2. distillationThe solvent was then distilled off under reduced pressure
3. additionTo that residue was added water
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with water
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-b146f024f5704eeeb15d3610c713a0b7

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06248766B1