Methyl iodide → Methyl 3-(2-methyl-1-oxopropan-2-yl)benzoate

Temperature

60 °C

To a solution of 3-(1,1-dimethyl-2-oxoethyl)benzoic acid (3.50 g, 18.2 mmol) in acetone (60 mL) were added potassium carbonate (3.78 g, 27.3 mmol) and methyl iodide (3.40 mL, 54.6 mmol), and the mixture was stirred at 60° C. for 5 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. To the obtained residue was added saturated aqueous sodium hydrogen carbonate solution (50 mL), and the mixture was extracted with ethyl acetate (100 mL, 30 mL). The combined organic layer was washed with saturated brine (20 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give methyl 3-(1,1-dimethyl-2-oxoethyl)benzoate as a yellow oil.

1. filtrationThe insoluble material was filtered off
2. concentrationthe filtrate was concentrated under reduced pressure
3. additionTo the obtained residue was added saturated aqueous sodium hydrogen carbonate solution (50 mL)
4. extractionthe mixture was extracted with ethyl acetate (100 mL, 30 mL)
5. washThe combined organic layer was washed with saturated brine (20 mL)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationThe insoluble material was filtered off
8. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-4e99005e7c5f42ff8bae21f1af5dc994

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2