1-Phenylcyclohexanol → 1-Phenylcyclohexene

HRID 1734962

Reaction equation

HRID 1734962 reaction equation
C(C1CCC(=O)CC1)CC.[2H]O[2H].C(OC1C=CC(Br)=CC=1)C.[C:24]1([C:30]2(O)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[C:24]1([C:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 153191-PhenylcyclohexanolHCID 24602Deuterium OxideHCID 685234-BromophenetoleHCID 1424824-Propylcyclohexanone

Product 1

HCID 130431-Phenylcyclohexene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Propylcyclohexanone is dissolved in a solvent, e.g., dichloromethane, and heated with heavy water (D2O) in the presence of a base to obtain 4-propylcyclohexanone-2,2,6,6-d4, which is then reacted with a Grignard reagent prepared from 1-ethoxy-4-bromobenzene. The resulting d4 -phenylcyclohexanol derivative is dehydrated to obtain a d3 -phenylcyclohexene derivative. The d3 -phenylcyclohexene derivative is catalytically reduced, and the cis-compound is removed to obtain 1-(trans-4-propylcyclohexyl-2,2,6-d3)-4-ethoxybenzene. ##STR60##

Workup

  1. customto obtain 4-propylcyclohexanone-2,2,6,6-d4, which

Sources & evidence

ORD record
ord-693aac6a46134b7f9e10d39df891da98
Source dataset
uspto-grants-1996_07
Patent number
US05536443

Linked notes

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