Salicylic Acid → Methyl 2-Methoxybenzoate

To a stirred solution of salicylic acid (50 g, 143 mmol) in acetone (300 mL) was added anhydrous powdered potassium carbonate (80 g, 580 mmol). Dimethyl sulfate (44.25 g, 290 mmol) was added in portions for about 10 min at room temperature. After the addition was complete, the solution was heated to reflux temperature on a water bath and maintained for 3 h. The solution was cooled to room temperature and then concentrated under reduced pressure. Distilled water (200 mL) was added to the reaction mixture, which was then extracted with ethyl acetate (200 mL). The organic layer was washed with distilled water (2×200 mL), dried over anhydrous sodium sulfate, and concentrated to yield the title Methyl 2-methoxy-benzoate (45 g, 80%).

1. additionAfter the addition
2. temperaturethe solution was heated
3. temperatureto reflux temperature on a water bath
4. temperaturemaintained for 3 h
5. concentrationconcentrated under reduced pressure
6. additionDistilled water (200 mL) was added to the reaction mixture, which
7. extractionwas then extracted with ethyl acetate (200 mL)
8. washThe organic layer was washed with distilled water (2×200 mL)
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated

ORD record

ord-eb03c09389fd4b20829ce12f35dcb352

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07332629B2