Hydrochloric Acid → 5-Acetyl-4-(adamantan-1-ylmethoxy)-2-fluorobenzoic acid

To a solution of methyl 5-acetyl-4-(adamantan-1-ylmethoxy)-2-fluorobenzoate (0.75 g, 2.10 mmol) in tetrahydrofuran (10 mL) was added a solution of lithium hydroxide monohydrate (0.441 g, 10.50 mmol) in water (4 mL) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 16 hours. After adjusting the reaction mixture to pH 2 with 1 N hydrochloric acid, the mixture was extracted with ethyl acetate (3×20 mL). The combined organic phase was washed with brine (5 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo yielded the title compound as a colorless oil (0.727 g, quant.), which was used without further purification: MS (ES−) m/z 345.3 (M−1).

1. extractionthe mixture was extracted with ethyl acetate (3×20 mL)
2. washThe combined organic phase was washed with brine (5 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationfiltered

ORD record

ord-2c23ac96afe146388b1f07914dd0d9cf

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952169B2