Acetophenone → HCID 54100420, compound

HRID 1649276Notes

Reaction equation

HRID 1649276 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-e36fe0d2cc104ecaba2a0172a62b458f
Source dataset
uspto-grants-1983_11
Patent number
US04415756

Reaction notes

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