Hydrochloric Acid → 3-(1-Cyano-1-methylethoxy)benzoic acid

To a solution of methyl 3-(1-cyano-1-methylethoxy)benzoate (2.07 g, 9.44 mmol) in methanol (12 ml)/tetrahydrofuran (4 mL) was added 2N aqueous sodium hydroxide solution (9.44 mL, 18.9 mmol), and the mixture was stirred at room temperature for 30 min. 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 (50 ml, 20 mL). The combined organic layer was washed with saturated brine (10 mL), and dried over anhydrous magnesium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=10/90→50/50), and a fraction containing the object product was concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate and n-hexane to give the title compound (1.01 g, 51%) as colorless crystals.

1. additionwas added
2. extractionthe mixture was extracted with ethyl acetate (50 ml, 20 mL)
3. washThe combined organic layer was washed with saturated brine (10 mL)
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationInsoluble material was filtered off
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=10/90→50/50)
8. additiona fraction containing the object product
9. concentrationwas concentrated under reduced pressure
10. customThe obtained residue was recrystallized from ethyl acetate and n-hexane

ORD record

ord-0526a6ae95d04d36bdba4093b5e3ff61

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08497274B2