Acetone → 4-(4-Fluorophenoxy)cyclohexan-1-one

HRID 1085681Notes

Reaction equation

HRID 1085681 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.CC(=O)C.S(=O)(=O)(O)O.CO>O.[O-2].[O-2].[O-2].[Cr+6]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH2:8][CH2:9][C:10](=[O:13])[CH2:11][CH2:12]2)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 1118Sulfuric AcidHCID 15725170HCID 15725170, compound

Product 1

HCID 157251714-(4-Fluorophenoxy)cyclohexan-1-oneYield 96.1%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

To a stirred and cooled mixture of 8.9 parts of 4-(4-fluorophenoxy)cyclohexanol and 160 parts of 2-propanone were added dropwise 13 parts of a solution of 26.7 parts of chromium trioxide in 42.3 parts of concentrate sulfuric acid diluted with water till a volume of 100 parts at a temperature below 5° C. Upon completion, stirring was continued for 3 hours at room temperature. After the addition of a few parts of methanol, the reaction mixture was poured onto water. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 8.4 parts (96.1%) of 4-(4-fluorophenoxy)cyclohexanone as a residue (140).

Workup

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. additionthe reaction mixture was poured onto water
  4. extractionThe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-bc68d69b61b94f7296f5af3d00c3911c
Source dataset
uspto-grants-1991_04
Patent number
US05010198

Reaction notes

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