Hydrochloric Acid → 1-(4-Fluorophenyl)-4-oxocyclohexanecarboxylic acid

HRID 1065270Notes

Reaction equation

HRID 1065270 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]([OH:20])=[O:19])[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:18]([OH:20])=[O:19])[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 122302461,4-Dioxaspiro[4.5]decane-8-carboxylic acid, 8-(4-fluorophenyl)-

Product 1

HCID 219553321-(4-Fluorophenyl)-4-oxocyclohexanecarboxylic acidYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 40 parts of 8-(4-fluorophenyl)-1,4-dioxaspiro[4,5]decane-8-carboxylic acid, 100 parts of a hydrochloric acid solution 6 N and 100 parts of acetic acid is started and refluxed overnight. The reaction mixture is cooled and the product is extracted with trichloromethane. The extract is washed three times with water, dried, filtered and evaporated, yielding 17 parts (50%) of 1-(4-fluorophenyl)-4-oxocyclohexanecarboxylic acid as a residue.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. extractionthe product is extracted with trichloromethane
  4. washThe extract is washed three times with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-308570129b6a45b1ac6ba068a10387fd
Source dataset
uspto-grants-1982_05
Patent number
US04329353

Reaction notes

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