Methanol → Methyl 4-hydroxy-2-methylbenzoate

Temperature

60 °C

To methanol (10 ml) was added dropwise thionyl chloride (1.92 ml, 26.3 mmol) at 0° C., 4-hydroxy-2-methylbenzoic acid (2.00 g, 13.1 mmol) was added, and the mixture was stirred at 60° C. overnight. After completion of the reaction, the solvent was evaporated, and the residue was dissolved in ethyl acetate (20 ml). The mixture was washed twice with 5% aqueous sodium hydrogen carbonate solution (10 ml), once with 1 mol/l hydrochloric acid (10 ml), and once with water (10 ml), and the solvent was evaporated to give methyl 4-hydroxy-2-methylbenzoate (2.24 g, yield 100%).

1. customAfter completion of the reaction
2. customthe solvent was evaporated
3. dissolutionthe residue was dissolved in ethyl acetate (20 ml)
4. washThe mixture was washed twice with 5% aqueous sodium hydrogen carbonate solution (10 ml), once with 1 mol/l hydrochloric acid (10 ml)
5. customonce with water (10 ml), and the solvent was evaporated

ORD record

ord-5b5e0a2312604e6bb337ea6a4ede85ee

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846885B2