Hydrochloric Acid → 3-(1,1-Dimethyl-2-oxoethyl)benzoic acid

Temperature

0 °C

To a solution of 3-(1-cyano-1-methylethyl)benzoic acid (8.60 g, 45.5 mmol) in toluene (60 mL)/tetrahydrofuran (40 mL) was added dropwise 1.0 M hexane solution (100 mL, 100 mmol) of diisobutylaluminum hydride at −78° C. over 1 hr. After the completion of the dropwise addition, the mixture was stirred at −78° C. for 1 hr and at 0° C. for 1 hr. The reaction mixture was poured into a mixture of ethyl acetate (200 mL) and 3N hydrochloric acid (300 mL), and the organic layer was separated from the aqueous layer. The aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layer was washed with saturated brine (50 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was crystallized from ethyl acetate/hexane to give the title compound (6.39 g, 73%) as colorless crystals.

1. additionAfter the completion of the dropwise addition
2. customthe organic layer was separated from the aqueous layer
3. extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
4. washThe combined organic layer was washed with saturated brine (50 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationThe insoluble material was filtered off
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe obtained residue was crystallized from ethyl acetate/hexane

ORD record

ord-1f8df4f42b074a1690d906cddad4ffc2

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324395B2