1-(3-(Trifluoromethoxy)phenyl)ethanone → 1-[3-(Trifluoromethoxy)phenyl]ethan-1-ol

HRID 912020Notes

Reaction equation

HRID 912020 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.O>[F:1][C:2]([F:13])([F:14])[O:3][C:4]1[CH:5]=[C:6]([CH:10]([OH:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 7371611-(3-(Trifluoromethoxy)phenyl)ethanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 448910721-[3-(Trifluoromethoxy)phenyl]ethan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(3-Trifluoromethoxyphenyl)ethanone (1.00 g, 4.90 mmol) in THF (5 mL) at 0° C. was added 1M LiAlH4 in THF (5.9 mL, 5.9 mmol), and the solution was allowed to warm to rt. A few drops of water were added to quench. The mixture was concentrated in vacuo, transferred to a separatory funnel, and extracted using DCM and sat. aq. Rochelle salt. The organic layer was concentrated in vacuo to afford the title compound as a clear oil.

Workup

  1. customto quench
  2. concentrationThe mixture was concentrated in vacuo
  3. customtransferred to a separatory funnel
  4. extractionextracted
  5. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-49adbfd6985c447db28fbb4e3494241a
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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