Dimethyl Ether → 4-Methoxy-4-phenylcyclohexanone

HRID 1816349Notes

Reaction equation

HRID 1816349 reaction equation
[CH3:1][O:2][C:3]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:12][CH2:11][C:6]2(OCC[O:7]2)[CH2:5][CH2:4]1.C(=O)([O-])O.[Na+].COC>O1CCCC1>[CH3:1][O:2][C:3]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:12][CH2:11][C:6](=[O:7])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8254Dimethyl EtherHCID 516892Sodium BicarbonateHCID 224929828-Methoxy-8-phenyl-1,4-dioxaspiro[4.5]decane

Product 1

HCID 224929924-Methoxy-4-phenylcyclohexanoneYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-methoxy-8-phenyl-1,4-dioxaspiro[4.5]decane (5.96 g) and 3N-hydrrochloric acid (24 ml) in tetrahydrofuran was stirred at room temperature for 24 hours. The reaction mixture was added to a mixture of sodium hydrogen carbonate solution and dimethyl ether. The organic layer was washed with sodium hydrogen carbonate solution and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (1:0-150:1 dichloromethane-methanol elution) to give 4-methoxy-4-phenylcyclohexanone (3.6 g).

Workup

  1. washThe organic layer was washed with sodium hydrogen carbonate solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe magnesium sulfate was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (1:0-150:1 dichloromethane-methanol elution)

Sources & evidence

ORD record
ord-7ee3d31164234e8698c29714a813150d
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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