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

HRID 1723431Notes

Reaction equation

HRID 1723431 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-b81178eb3b7b465a9ff17f79abd8d97f
Source dataset
uspto-grants-1989_08
Patent number
US04861785

Reaction notes

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