Lithium Hydroxide → 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 a mixture of THF (40 mL)/water (20 mL)/MeOH (20 mL) and 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 concentrated in vacuo. The residue was dissolved in water and cooled to 0° C. and treated with 1 M HCl solution (to pH 3). The resulting precipitate was filtered, 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); 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. additionwas added
2. temperatureThe reaction mixture was cooled to room temperature
3. concentrationthe concentrated in vacuo
4. dissolutionThe residue was dissolved in water
5. temperaturecooled to 0° C.
6. additiontreated with 1 M HCl solution (to pH 3)
7. filtrationThe resulting precipitate was filtered
8. washwashed with water
9. customdried under high vacuum

ORD record

ord-aea6f56ddd2f4fd3b5460e9a38038560

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828996B2