Water → 2-Hydroxy-4-(trifluoromethyl)benzenemethanol

To a solution of 600 mg (2.91 mmol) of 2-hydroxy-4-trifluoromethyl-benzoic acid in THF (3 ml) were added dropwise 5.82 ml of a 1 molar solution of BH3-THF complex in THF at 0° C. After the reaction mixture was stirred for 18 h at RT, water was added to destroy excess reducing agent. Then 15 ml of 2N NaOH-solution were added and the mixture was stirred for 30 min. Then ether (10 ml) was added and the aqueous phase was separated. The volatile solvents of the organic phase were removed and the remaining residue was combined with the aqueous phase. The pH of the aqueous phase was then carefully adjusted to 6-7 by addition of dilute acetic acid at 0° C. and the mixture was extracted with ether. The combined extracts were then dried (MgSO4) and concentrated to yield 649 mg (93%) of crude 2-hydroxymethyl-5-trifluoromethyl-phenol (purity ˜80%) as a light yellow oil. MS (ISP) 191.2 (M−H)−.

1. customto destroy excess
2. additionThen 15 ml of 2N NaOH-solution were added
3. stirringthe mixture was stirred for 30 min
4. additionThen ether (10 ml) was added
5. customthe aqueous phase was separated
6. customThe volatile solvents of the organic phase were removed
7. additionThe pH of the aqueous phase was then carefully adjusted to 6-7 by addition of dilute acetic acid at 0° C.
8. extractionthe mixture was extracted with ether
9. dry with materialThe combined extracts were then dried (MgSO4)
10. concentrationconcentrated

ORD record

ord-c77c7c27022e4bde9f8999a57c206c6c

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07674815B2