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 a 1.0M solution of diisobutylaluminum hydride in hexane (100 mL, 100 mmol) 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 and the aqueous layer were separated and 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 recrystallized from ethyl acetate and 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 and the aqueous layer were separated
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 recrystallized from ethyl acetate and hexane

ORD record

ord-9151ddc994d04397bd86ef21a4e3ca9b

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2