Acetone → 4-Methoxy-4-(methoxymethyl)cyclohexanone

HRID 930960Notes

Reaction equation

HRID 930960 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.CC(C)=O.O.CC1C=CC(S(O)(=O)=O)=CC=1>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 3

HCID 180AcetoneHCID 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 1

HCID 962WaterSolvent

Procedure

A mixture comprising 217 g (1.00 mol) 8-methoxy-8-(methoxymethyl)-1,4-dioxaspiro[4.5]decane (prepared according to intermediate example 16e), 1.7 L acetone, 0.86 L water and 30.5 g 4-methylbenzenesulfonic acid hydrate was stirred at 23° C. overnight. The acetone was removed, 0.5 L saturated aqueous sodium hydrogencarbonate added followed by 0.4 L brine. The mixture was extracted with ethyl acetate, the combined organic layers were washed with brine and dried over sodium sulfate. After filtration and removal of the solvent 180 g (max. 100%) of the title compound were obtained that was used without further purification.

Workup

  1. customThe acetone was removed
  2. addition0.5 L saturated aqueous sodium hydrogencarbonate added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration and removal of the solvent 180 g (max. 100%) of the title compound
  7. customwere obtained
  8. customthat was used without further purification

Sources & evidence

ORD record
ord-f7315733175b45699d7356835f2c2b5b
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

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