Ammonium Chloride → alpha-Methyl-4-(trifluoromethoxy)benzenemethanol

A cooled (0° C.) solution of 4-(trifluoromethoxy)benzaldehyde (3.000 g; 15.78 mmol) in anh. THF (50 ml) was treated dropwise with a solution of methylmagnesium bromide (3 M in Et2O; 6.30 ml; 18.90 mmol), and the resulting mixture was stirred at rt, under nitrogen, for 4 h. The resulting reaction mixture was cooled to 0° C., and aq. sat. NH4Cl (30 ml) was added dropwise. The separated aq. layer was further extracted with AcOEt (3×20 ml), and the mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=40/1) afforded 1-(4-(trifluoromethoxy)phenyl)ethanol as a colorless oil. LC-MS (conditions D): tR=0.88 min.; no ionisation.

1. customThe resulting reaction mixture
2. temperaturewas cooled to 0° C.
3. extractionThe separated aq. layer was further extracted with AcOEt (3×20 ml)
4. dry with materialthe mixed organic layers were dried over anh. MgSO4
5. filtrationfiltered
6. concentrationconcentrated to dryness under reduced pressure
7. customPurification by FC (DCM/MeOH=40/1)

ORD record

ord-72207d918d7a46eda977840cd5127025

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242970B2