1-Phenylcyclohexanol → 1-Phenylcyclohexene

HRID 2259531

Reaktionsgleichung

Reaktionsgleichung von HRID 2259531
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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 130431-Phenylcyclohexene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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##

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-0d7b5b94b4fb41579b124c2b6a7c6515
Quelldatensatz
uspto-grants-1995_12
Patentnummer
US05474707

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