Methanol → HCID 68153645, compound

Temperature

55 °C

Methyl 3-fluoro-4-(2-hydroxy-2-methyl-propyl)benzoate (1.59 g, 7.03 mmol) was dissolved in THF (40 mL), water (200 mL) and MeOH (21 mL) before LiOH (1.01 g, 42.2 mmol) was added. The reaction mixture was heated at 55° C. for 30 minutes. The reaction mixture was cooled to room temperature and the solvents were removed under reduced pressure. The residue was dissolved in water and cooled in an ice water bath and treated with HCl 1M to pH 3. The resulting precipitate was collected by vacuum filtration, washed with water and dried under high vacuum to yield 3-fluoro-4-(2-hydroxy-2-methyl-propyl)benzoic acid (999 mg, 67%) as a white solid. ESI-MS m/z calc. 212.1, found 211.1 (M+1)+; Retention time: 0.98 minutes (3 min run, scanned using negative ionization mode). 1H NMR (400 MHz, CDCl3) δ 7.84 (dd, J=7.9, 1.6 Hz, 1H), 7.77 (dd, J=10.1, 1.6 Hz, 1H), 7.39 (d, J=15.1 Hz, 1H), 2.91 (s, 2H), 1.28 (s, 6H).

1. temperatureThe reaction mixture was cooled to room temperature
2. customthe solvents were removed under reduced pressure
3. dissolutionThe residue was dissolved in water
4. temperaturecooled in an ice water bath
5. additiontreated with HCl 1M to pH 3
6. filtrationThe resulting precipitate was collected by vacuum filtration
7. washwashed with water
8. customdried under high vacuum

ORD record

ord-bbe07aeb4e6448da9a8d1680c40df479

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916565B2