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-87adeb2e0f5c47d6896e79c4f38b82ed

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08470866B2