Cornforth reagent → 1-[2-Hydroxy-5-(trifluoromethoxy)phenyl]ethan-1-one

HRID 1463279Notes

Reaction equation

HRID 1463279 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([CH:11]([OH:13])[CH3:12])[CH:5]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]([F:14])([F:15])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11](=[O:13])[CH3:12])[CH:5]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 18987737HCID 18987737, compound

Product 1

HCID 27751021-[2-Hydroxy-5-(trifluoromethoxy)phenyl]ethan-1-oneYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 20 ml of dichloromethane was dissolved 0.85 g (3.83 mmole) of the compound obtained in step 1; and, a suitable amount of Cellite and 1.73 g (4.6 mmole) of pyridinium dichromate were added thereto. The resultant mixture was stirred for 30 minutes at room temperature and filtered by a Cellite layer to obtain precipitates, which were purified by silica gel column chromatography using as an eluent a mixture of hexane and ethyl acetate of 6:1 and then concentrated under reduced pressure at 0° C. to obtain 0.72 g (yield 85%) of the title compound.

Workup

  1. filtrationfiltered by a Cellite layer
  2. customto obtain
  3. customprecipitates
  4. customwhich were purified by silica gel column chromatography
  5. additiona mixture of hexane and ethyl acetate of 6:1
  6. concentrationconcentrated under reduced pressure at 0° C.

Sources & evidence

ORD record
ord-fb06f018bfc547be9941dd595469b47c
Source dataset
uspto-grants-1994_04
Patent number
US05300511

Reaction notes

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