Sodium Hydroxide → 1-Cyclohexyloxy-hex-5-en-2-one

HRID 6500Notes

Reaction equation

HRID 6500 reaction equation
[CH:1]1([O:7][CH2:8][C:9]([CH:11]([CH2:17][CH:18]=[CH2:19])C(OCC)=O)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CCOCC>[CH:1]1([O:7][CH2:8][C:9](=[O:10])[CH2:11][CH2:17][CH:18]=[CH2:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19793910Ethyl 2-(cyclohexyloxyacetyl)-4-pentenoate

Product 1

HCID 197939121-Cyclohexyloxy-hex-5-en-2-oneYield 58.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

140 g of ethyl 2-(cyclohexyloxyacetyl)-4-pentenoate are heated under reflux in 650 g of 5% strength aqueous sodium hydroxide solution for 4 hours. 500 ml of ether are added to the reaction mixture. The organic phase is separated off and concentrated and the residue is distilled. About 60 g of 1-cyclohexyloxy-hex-5-en-2-one are obtained. (Temperature (bottom)=115°-155° C., temperature (top)=83° C.; 0.8 mbar).

Workup

  1. customThe organic phase is separated off
  2. concentrationconcentrated
  3. distillationthe residue is distilled

Sources & evidence

ORD record
ord-65ad894ecf63452786d85d75967b1990
Source dataset
uspto-grants-1993_09
Patent number
US05248831

Reaction notes

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