p-Toluenesulfonic acid monohydrate → 4-Methoxy-4-(trifluoromethyl)cyclohexan-1-one

HRID 922120Notes

Reaction equation

HRID 922120 reaction equation
[CH3:1][O:2][C:3]1([C:13]([F:16])([F:15])[F:14])[CH2:12][CH2:11][C:6]2(OCC[O:7]2)[CH2:5][CH2:4]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[CH3:1][O:2][C:3]1([C:13]([F:14])([F:15])[F:16])[CH2:4][CH2:5][C:6](=[O:7])[CH2:11][CH2:12]1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 712468178-Methoxy-8-(trifluoromethyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 894014664-Methoxy-4-(trifluoromethyl)cyclohexan-1-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

11.80 g (49.12 mmol) of 8-methoxy-8-(trifluoromethyl)-1,4-dioxaspiro[4.5]decane (Example 9A) were dissolved in 236 ml of acetone and 118 ml of water, 1.50 g (7.86 mmol) of 4-toluenesulphonic acid monohydrate were added and the mixture was heated at reflux overnight. The mixture was then poured into 1.2 l of water and the product was extracted with diethyl ether. The organic phase was washed with water, dried over sodium sulphate and concentrated under reduced pressure. The resulting residue was distilled under reduced pressure (boiling point: 106-110° C. at 40 mbar). This gave 6.86 g (71% of theory) of the title compound as a yellowish oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. extractionthe product was extracted with diethyl ether
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. distillationThe resulting residue was distilled under reduced pressure (boiling point: 106-110° C. at 40 mbar)

Sources & evidence

ORD record
ord-85c9c50769a94a8da60ee05842c2430a
Source dataset
uspto-grants-2016_03
Patent number
US09278925B2

Reaction notes

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