Water → Ethyl 4-hydroxy-4-methylcyclohexane-1-carboxylate

HRID 1245441Notes

Reaction equation

HRID 1245441 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.O.[CH2:14](OCC)C>>[OH:1][C:2]1([CH3:14])[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 21911966Ethyl 4-hydroxy-4-methylcyclohexane-1-carboxylate

Conditions

Temperature
-60 °C

Procedure

To a solution of 25.0 g of ethyl 4-oxocyclohexanecarboxylate in 500 ml of diethyl ether, 150 ml of 1.6N methyl lithium-ether solution was added at −60° C. in nitrogen atmosphere, followed by 30 minutes' stirring at −60° C. Water was added to the reaction liquid which then was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried on anhydrous magnesium sulfate and the solvent was distilled off. The residue was separated and purified on silica gel column chromatography (ethyl acetate/hexane=1/4) to provide 22.7 g of the title compound.

Workup

  1. extractionthen was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried on anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was separated
  6. custompurified on silica gel column chromatography (ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-1198ecdc0357451ebd69f0142c895c20
Source dataset
uspto-grants-2006_10
Patent number
US07125877B2

Reaction notes

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