2,2,2-Trifluoro-1-(2-methoxyphenyl)ethanone → 2,2,2-Trifluoro-1-(2-methoxyphenyl)ethanol

HRID 859648Notes

Reaction equation

HRID 859648 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])=[O:4]>[Pd].CO>[F:1][C:2]([F:13])([F:14])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])[OH:4]

Participants

4

Reactant 1

HCID 27597332,2,2-Trifluoro-1-(2-methoxyphenyl)ethanone

Product 1

HCID 28292482,2,2-Trifluoro-1-(2-methoxyphenyl)ethanolYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (1.5 g) was added to a solution of 2,2,2-trifluoro-1-(2-methoxyphenyl)ethanone (3.0 g) in methanol (50 ml). The resultant was hydrogenated at room temperature for 12 hrs. After which time the catalyst was filtered off through a plug of celiteand the solvent concentrated in vacuuo. The crude was purified by column chromatography on silica gel eluting with 100% hexanes the 80:20 hexanes:ethylacetate to afford the title compound as a yellow oil (3.0 g). 1H NMR (CDCl3): δ 3.75 (d, J=2.56 Hz, 1 H), 3.96 (s, 3 H), 5.35 (m,1 H), 7.05 (m, 2 H), 7.50 (m, 2 H).

Workup

  1. filtrationAfter which time the catalyst was filtered off through a plug of celiteand the solvent
  2. concentrationconcentrated in vacuuo
  3. customThe crude was purified by column chromatography on silica gel eluting with 100% hexanes the 80:20 hexanes

Sources & evidence

ORD record
ord-2c21f1a105a845c5804389094be5114a
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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