Acetophenone → HCID 54100420, compound

HRID 1263011Notes

Reaction equation

HRID 1263011 reaction equation
[CH2:1]([C:5]12[CH2:12][CH2:11][CH:8]([CH:9]=[CH:10]1)[CH2:7][C:6]2=[O:13])[CH2:2][CH2:3][CH3:4].C(C1C=CC=CC=1)(=O)C>C1CCCCC1>[CH2:1]([C:5]12[CH:9]3[CH:8]([CH2:7][C:6](=[O:13])[CH:10]13)[CH2:11][CH2:12]2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 20452055HCID 20452055, compound

Product 1

HCID 54100420HCID 54100420, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A 4% solution of (+)-1-butyl-bicyclo[2.2.2]oct-5-en-2-one (1.5 g.) in cyclohexane was irradiated in a Pyrex apparatus under argon and in the presence of 200 mg. of acetophenone with a 250 w. medium pressure mercury lamp. After 50 hours, a conversion of 98% was achieved. The solution was concentrated by evaporation and the residue subjected to chromatography on 100 g. of silica gel (70 to 230 mesh) with toluene to remove the acetophenone and with toluene/1% diethyl ether. Pure (-)-8-butyl-tricyclo[3.3.0.02,8 ]octan-3-one was obtained.

Workup

  1. concentrationThe solution was concentrated by evaporation
  2. customof silica gel (70 to 230 mesh) with toluene to remove the acetophenone

Sources & evidence

ORD record
ord-86f81125f5444b789723442d442e467e
Source dataset
uspto-grants-1984_06
Patent number
US04454352

Reaction notes

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