Methanol → Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

A mixture of 2-hydroxy-4-methylbenzoic acid (100.0 g, 657.2 mmol), concentrated sulfuric acid (50 mL) in methanol (1000 mL) was refluxed for 20 hours under nitrogen atmosphere. The resulting mixture was concentrated in vacuo. The residue was poured into ice-water, extracted with ethyl acetate (1000 mL). The organic layer was washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, concentrated in vacuo to afford 109 g of the crude product of methyl 2-hydroxy-4-methylbenzoate as light brown oil, which was used directly in the next step without further purification.

1. temperaturewas refluxed for 20 hours under nitrogen atmosphere
2. concentrationThe resulting mixture was concentrated in vacuo
3. additionThe residue was poured into ice-water
4. extractionextracted with ethyl acetate (1000 mL)
5. washThe organic layer was washed with saturated sodium bicarbonate, brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated in vacuo

ORD record

ord-e3f00ed591544f0fa26331d328411137

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871756B2