p-Toluenesulfonic acid monohydrate → 4-Methoxy-4-(methoxymethyl)cyclohexanone

HRID 922121Notes

Reaction equation

HRID 922121 reaction equation
[CH3:1][O:2][C:3]1([CH2:13][O:14][CH3:15])[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([CH2:13][O:14][CH3:15])[CH2:4][CH2:5][C:6](=[O:7])[CH2:11][CH2:12]1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 712474008-Methoxy-8-(methoxymethyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 857431314-Methoxy-4-(methoxymethyl)cyclohexanone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

13.3 g (61.5 mmol) of the compound from Example 10A were dissolved in 200 ml of acetone and 100 ml of water, 1.87 g (9.84 mmol) of 4-toluenesulphonic acid monohydrate were added and the mixture was stirred at room temperature for two days. The acetone was then distilled off, the aqueous residue was neutralized by addition of sodium bicarbonate and 23.2 g of sodium chloride were added. The mixture was extracted repeatedly with ethyl acetate and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated. This gave 10.3 g (97% of theory) of the title compound.

Workup

  1. distillationThe acetone was then distilled off
  2. additionthe aqueous residue was neutralized by addition of sodium bicarbonate and 23.2 g of sodium chloride
  3. additionwere added
  4. extractionThe mixture was extracted repeatedly with ethyl acetate
  5. washthe combined organic phases were washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5620cb49020c45ec96805aaef14feff6
Source dataset
uspto-grants-2016_03
Patent number
US09278925B2

Reaction notes

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