Hydrogen Bromide → 2-Phenyl-2-cyclohexen-1-one

HRID 273762

Reaction equation

HRID 273762 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]1=[O:14].Br>C(OCCCC)CCC>[C:8]1([C:4]2[C:3](=[O:14])[CH2:2][CH2:7][CH2:6][CH:5]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 127791292-Bromo-6-phenylcyclohexanone

Product 1

HCID 12014012-Phenyl-2-cyclohexen-1-oneYield 80%

Reagents, catalysts & solvents 1

HCID 8909Butyl etherSolvent

Procedure

A suspension of 4.97 g (19.6 mmole) of 2-bromo-6-phenylcyclohexanone in 120 mL of di-n-butyl ether was heated at 175° C. for 7 hours, at which point evolution of gaseous HBr had essentially ceased. The mixture was concentrated in vacuo and the residue purified by flash chromatography with 75:25 methylene chloride: hexanes to provide 2.69 g (80%) of a white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue purified by flash chromatography with 75:25 methylene chloride

Sources & evidence

ORD record
ord-edfe22590e604754beb43689d11c139e
Source dataset
uspto-grants-1995_02
Patent number
US05387595

Linked notes

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