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

To a solution of 3-(1,1-dimethyl-2-oxoethyl)benzoic acid 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 hydrogencarbonate 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 hydrogencarbonate 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-f95fdac6cfc74cd7a4ac0b1e16d118e5

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324395B2