(2E)-2-(hydroxymethylene)-4,4-dimethylcyclohexanone → (2E)-1-(4-chlorophenyl)-2-(hydroxymethylene)-4,4-dimethylcyclohexanol

HRID 1920288Notes

Reaction equation

HRID 1920288 reaction equation
[OH:1]/[CH:2]=[C:3]1/[C:4](=[O:11])[CH2:5][CH2:6][C:7]([CH3:10])([CH3:9])[CH2:8]/1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([Mg]Br)=[CH:15][CH:14]=1>>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:4]2([OH:11])[CH2:5][CH2:6][C:7]([CH3:9])([CH3:10])[CH2:8]/[C:3]/2=[CH:2]\[OH:1])=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 12173050(2E)-2-(hydroxymethylene)-4,4-dimethylcyclohexanoneHCID 178478191HCID 178478191, compound

Product 1

HCID 67079188(2E)-1-(4-chlorophenyl)-2-(hydroxymethylene)-4,4-dimethylcyclohexanol

Procedure

reacting the first protected (2E)-2-(hydroxymethylene)-4,4-dimethylcyclohexanone and 4-chlorophenyl magnesium bromide to provide the first protected (2E)-1-(4-chlorophenyl)-2-(hydroxymethylene)-4,4-dimethylcyclohexanol; and isolating or not isolating the first protected (2E)-1-(4-chlorophenyl)-2-(hydroxymethylene)-4,4-dimethylcyclohexanol; and

Sources & evidence

ORD record
ord-d7b749e8517443e0a5ccf415758ab440
Source dataset
uspto-grants-2012_05
Patent number
US08168784B2

Reaction notes

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