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) under stirring at room temperature, and the mixture was stirred at 80° C. for 7 hr. To the reaction mixture were added 2-bromopropane (1.79 mL, 19.1 mmol) and potassium iodide (0.27 g, 1.59 mmol), and the mixture was further stirred at 80° C. for 15 hr. The reaction mixture was allowed to cool, diluted with ethyl acetate, 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.

1. stirringthe mixture was stirred at 80° C. for 7 hr
2. stirringthe mixture was further stirred at 80° C. for 15 hr
3. temperatureto cool
4. washwashed 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-bb2981a1466248789bf2abd202a571d1

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07786165B2