p-Toluenesulfonic acid → 4-(4-Fluorophenyl)-4-methoxycyclohexanone

HRID 273738Notes

Reaction equation

HRID 273738 reaction equation
[CH3:1][O:2][C:3]1([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:12][CH2:11][C:6]2(OCC[O:7]2)[CH2:5][CH2:4]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.C([O-])(O)=O.[Na+]>[F:19][C:16]1[CH:15]=[CH:14][C:13]([C:3]2([O:2][CH3:1])[CH2:4][CH2:5][C:6](=[O:7])[CH2:11][CH2:12]2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 571381988-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol methyl ether

Product 1

HCID 184002134-(4-Fluorophenyl)-4-methoxycyclohexanoneYield 94%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 8-(4-fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol methyl ether in acetone (200 ml) was stirred for 96 hr with p-toluenesulfonic acid (0.1 g) and the solution diluted with saturated NaHCO3 solution. The mixture was concentrated in vacuo and the residue suspended in water. The mixture was extracted with ether and the ether extracts dried and concentrated in vacuo. The residue was crystallized from hexane to give 4-(4-fluoro-phenyl)-4-methoxycyclohexanone (94%, mp: 57°-59° C.).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionThe mixture was extracted with ether
  3. dry with materialthe ether extracts dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-45089b3689cf4fbb93bf8fde23d721bb
Source dataset
uspto-grants-1995_02
Patent number
US05387593

Reaction notes

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