Hydrochloric Acid → 3-(2-Methylbut-3-yn-2-yl)benzoic acid

Temperature

60 °C

To a solution of methyl 3-(1,1-dimethylprop-2-yn-1-yl)benzoate (2.26 g, 11.2 mmol) in methanol (15 mL)/tetrahydrofuran (10 mL) was added 2N aqueous sodium hydroxide solution (11.2 mL, 22.4 mmol), and the mixture was stirred at 60° C. for 3 hr. The reaction mixture was neutralized with 6N hydrochloric acid (5 mL), 1N hydrochloric acid (50 mL) was added, and the mixture was extracted with ethyl acetate (100 mL, 20 mL). The combined organic layer was washed with saturated brine (10 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 (1.94 g, 92%) as colorless crystals.

1. additionwas added
2. extractionthe mixture was extracted with ethyl acetate (100 mL, 20 mL)
3. washThe combined organic layer was washed with saturated brine (10 mL)
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationThe insoluble material was filtered off
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe obtained residue was recrystallized from ethyl acetate and hexane

ORD record

ord-cdbbe120a2f74130b44d6d4547b2f0f0

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2