Ammonium Chloride → 1-(4-(Trifluoromethoxy)phenyl)propan-1-ol

A cooled (0° C.) solution of 4-(trifluoromethoxy)benzaldehyde (5.000 g; 26.29 mmol) in anh. THF (50 ml) was treated dropwise with a solution of ethylmagnesium bromide (3 M in Et2O; 10.50 ml; 31.50 mmol), and the resulting mixture was stirred at rt, under nitrogen, for 17 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=60/1) afforded 1-(4-(trifluoromethoxy)phenyl)propan-1-ol as a colorless oil. LC-MS (conditions A): tR=0.79 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=60/1)

ORD record

ord-08ad95d6ed974d70b34f0764a6a21dae

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242970B2