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

Temperature

75 °C

To a 500 mL round bottom equipped with an Airflux Condenser and stir bar was added 2-methyl-3-(trifluoromethyl)benzoic acid (30 g, 147 mmol). The solid was taken up in Methanol (101 ml) and to that solution was slowly added sulfuric acid (8.22 ml, 154 mmol). The reaction was then fitted with the condenser and heated to 75° C. overnight. The reaction was cooled back to room temperature, and neutralized by slow addition of 1N NaOH (˜155 mL). The solution was then extracted with 3×300 mL Et2O, the organic layer dried over magnesium sulfate, and concentrated to an oil, which solidified under vacuum to give off white solid methyl 2-methyl-3-(trifluoromethyl)benzoate (28.25 g, 129 mmol, 88% yield) 1H NMR (400 MHz, DMSO-d6) δ ppm 2.54 (d, J=1.77 Hz, 3H) 3.89 (s, 3H) 7.53 (t, J=7.83 Hz, 1H) 7.89 (d, J=7.83 Hz, 1H) 7.97 (d, J=7.83 Hz, 1H).

1. customTo a 500 mL round bottom equipped with an Airflux Condenser
2. customThe reaction was then fitted with the condenser
3. temperatureThe reaction was cooled back to room temperature
4. extractionThe solution was then extracted with 3×300 mL Et2O
5. dry with materialthe organic layer dried over magnesium sulfate
6. concentrationconcentrated to an oil, which

ORD record

ord-6214d59bf0ce4ebd85438c384756db5f

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410095B2