Methanol → Methyl 2-methyl-3-(trifluoromethyl)benzoate

To a solution of 2-methyl-3-trifluoromethyl-benzoic acid (Apollo, 1 g, 4.90 mmol) in methanol (20 mL) was added concentrated sulfuric acid (0.5 mL) and the resulting mixture was heated to reflux overnight. The cooled reaction mixture was concentrated and diluted with water (25 mL) and a saturated sodium bicarbonate solution (25 mL). The mixture was extracted with ethyl acetate (50 mL), the organic phases combined, washed with water and dried over magnesium sulfate. The mixture was filtered and evaporated to give 2-methyl-3-trifluoromethyl-benzoic acid methyl ester (0.95 g, 4.35 mmol, 89%); 1H NMR (300 MHz, CDCl3) δ ppm 2.65 (s, 3H), 3.94 (s, 3H), 7.35 (t, J=7.85 Hz, 1H), 7.72-8.01 (m, 2H).

1. temperaturethe resulting mixture was heated
2. temperatureto reflux overnight
3. customThe cooled reaction mixture
4. concentrationwas concentrated
5. additiondiluted with water (25 mL)
6. extractionThe mixture was extracted with ethyl acetate (50 mL)
7. washwashed with water
8. dry with materialdried over magnesium sulfate
9. filtrationThe mixture was filtered
10. customevaporated

ORD record

ord-8644e95ba35f4b13821684c09a2a112c

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697705B2