Ethyl formate → (2E)-2-(hydroxymethylene)-4,4-dimethylcyclohexanone

HRID 1920356Notes

Reaction equation

HRID 1920356 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[CH:10](OCC)=[O:11].CC(C)([O-])C.[K+]>>[OH:11]/[CH:10]=[C:4]1/[C:5](=[O:8])[CH2:6][CH2:7][C:2]([CH3:9])([CH3:1])[CH2:3]/1

Participants

4

Reactant 3

HCID 8025Ethyl formateHCID 138166Cyclohexanone, 4,4-dimethyl-HCID 23665647Potassium tert-butoxide

Product 1

HCID 12173050(2E)-2-(hydroxymethylene)-4,4-dimethylcyclohexanone

Procedure

reacting 4,4-dimethylcyclohexanone, ethyl formate and potassium tert-butoxide at about −10° C. to about 0° C. to provide (2E)-2-(hydroxymethylene)-4,4-dimethylcyclohexanone and isolating or not isolating the (2E)-2-(hydroxymethylene)-4,4-dimethylcyclohexanone;

Workup

  1. customat about −10° C. to about 0° C.

Sources & evidence

ORD record
ord-2c12adb353b04c5eb45feaeb5965b7b3
Source dataset
uspto-grants-2012_05
Patent number
US08168784B2

Reaction notes

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