HCID 20346001, compound → 2-Methyl-1-[4-(pentafluoroethoxy)phenyl]propan-1-one

HRID 441901Notes

Reaction equation

HRID 441901 reaction equation
[CH:1]([CH:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[CH:8][CH:7]=1)[OH:5])([CH3:3])[CH3:2]>[O-2].[O-2].[O-2].[Cr+6].C(O)(=O)C>[F:18][C:13]([F:19])([O:12][C:9]1[CH:10]=[CH:11][C:6]([C:4]([CH:1]([CH3:2])[CH3:3])=[O:5])=[CH:7][CH:8]=1)[C:14]([F:15])([F:17])[F:16]

Participants

4

Reactant 1

HCID 20346001HCID 20346001, compound

Product 1

HCID 137279712-Methyl-1-[4-(pentafluoroethoxy)phenyl]propan-1-one

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent

Procedure

The preparation of pentafluoroethoxy-substituted phenyl alkyl ketones is accomplished following the procedure of Belous et al., J. Org. Chem. (U.S.S.R.) 7, 1521 (1971). According to that procedure, p-bromophenol is allowed to react with trifluoroacetic anhydride in the presence of sulfur tetrafluoride and hydrogen fluoride, to yield pentafluoroethoxy-4-bromobenzene. This compound is allowed to react with isobutyraldehyde in the presence of n-butyllithium to yield the intermediate alcohol, isopropyl p-(pentafluoroethoxy)phenyl carbinol. This alcohol is oxidizied with chromium trioxide in the presence of aqueous acetic acid to yield the ketone, isopropyl p-(pentafluoroethoxy)phenyl ketone.

Sources & evidence

ORD record
ord-d4729c8ad6d1485f8b03f967e4f6056a
Source dataset
uspto-grants-1977_08
Patent number
US04043791

Reaction notes

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