Hydrochloric Acid → Methyl Benzoate

To a cooled (0° C.) solution of 27 mg (1.17 m atoms) of sodium in 4 ml of absolute methanol there were added 78 mg (0.47 mmol) of methyl thiosalicylate. After stirring 5 minutes, a solution of 128 mg (0.39 mmol) of the foregoing mesylate in 3 ml of methanol was added. The reaction mixture was stirred at room temperature for 1 hour, diluted with 5 ml of water, acidified with 10% hydrochloric acid, and extracted with methylene chloride (3×6 ml). The combined extracts were washed with brine (5 ml), dried and evaporated in vacuo. The residue was purified by thin layer chromatography, using hexane-ethyl acetate (95:5) as gradient, to afford the title compound, as an oil.

1. stirringThe reaction mixture was stirred at room temperature for 1 hour
2. extractionextracted with methylene chloride (3×6 ml)
3. washThe combined extracts were washed with brine (5 ml)
4. customdried
5. customevaporated in vacuo
6. customThe residue was purified by thin layer chromatography

ORD record

ord-9c5a5879705e497183eec24a57800ccb

Source dataset

uspto-grants-1987_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04670465