Hydrochloric Acid → 4-(4-Fluorophenyl)cyclohexan-1-one

HRID 1065271Notes

Reaction equation

HRID 1065271 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.C(O)C.S(=O)(=O)(O)O>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1118Sulfuric AcidHCID 128344048-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 128343224-(4-Fluorophenyl)cyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 160 parts of 8-(4-fluorophenyl)-1,4-dioxaspiro[4,5]decane, 72 parts of hydrochloric acid, 800 parts of ethanol and 800 parts of water is stirred and refluxed for 2 h. 30. Then there are added dropwise 72 parts of sulfuric acid. Upon completion, stirring is continued at reflux temperature for one hour. The reaction mixture is cooled, poured onto water and the product is extracted with trichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is fractionated, yielding 68.5 parts of 4-(4-fluorophenyl)cyclohexanone; b.p. 110° C. at 1 mm. pressure.

Workup

  1. temperaturerefluxed for 2 h
  2. stirringUpon completion, stirring
  3. temperatureat reflux temperature for one hour
  4. temperatureThe reaction mixture is cooled
  5. additionpoured onto water
  6. extractionthe product is extracted with trichloromethane
  7. washThe extract is washed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-a8773da2509f44e185d1e760e1820c4b
Source dataset
uspto-grants-1982_05
Patent number
US04329353

Reaction notes

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