Acetic Acid → 1-Methoxy-1,1'-bicyclohexane-4-one

HRID 1816764Notes

Reaction equation

HRID 1816764 reaction equation
[CH:1]1([C:7]2([O:17][CH3:18])[CH2:16][CH2:15][C:10]3(OCC[O:11]3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=O)C.C(=O)([O-])O.[Na+].C(OCC)C>O>[CH3:18][O:17][C:7]1([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:16][CH2:15][C:10](=[O:11])[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 224947668-Cyclohexyl-8-methoxy-1,4-dioxaspiro[4.5]decane

Product 1

HCID 224929241-Methoxy-1,1'-bicyclohexane-4-oneYield 107.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8-cyclohexyl-8-methoxy-1,4-dioxaspiro[4.5]decane (1.15 g) and acetic acid (40 ml) in water was stirred at 100° C. for 6 hours. After cooling to room temperature, the reaction mixture was added to a mixture of sodium hydrogen carbonate solution and diethyl ether. The organic layer was taken, 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 to give 1-methoxy-1,1′-bicyclohexane-4-one (1.018 g).

Workup

  1. washwashed 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

Sources & evidence

ORD record
ord-b6fc3e30c9844efebb1d782acaae039c
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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