Potassium Iodide → Methyl 3-isopropoxy-4-methylbenzoate

To a mixture of methyl 3-hydroxy-4-methylbenzoate (5.28 g, 31.8 mmol), potassium carbonate (6.59 g, 47.7 mmol) and N,N-dimethylformamide (50 mL) were added 2-bromopropane (3.58 mL, 38.2 mmol) and potassium iodide (0.53 g, 3.18 mmol) with stirring at room temperature, and the mixture was stirred at 80° C. for 7 hr. 2-Bromopropane (1.79 mL, 19.1 mmol) and potassium iodide (0.27 g, 1.59 mmol) were added to the reaction mixture, and the mixture was further stirred at 80° C. for 15 hr. The reaction mixture was cooled, and diluted with ethyl acetate. The mixture washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=19/1-hexane/ethyl acetate=4/1) to give the title compound (6.3 g, yield 96%) as a colorless oil. MS (ESI+): 209 (M+H).

1. stirringthe mixture was stirred at 80° C. for 7 hr
2. stirringthe mixture was further stirred at 80° C. for 15 hr
3. temperatureThe reaction mixture was cooled
4. washThe mixture washed with water and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=19/1-hexane/ethyl acetate=4/1)

ORD record

ord-94f4bfe2b786476b80ce4dcf217da9c9

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517910B2