2-Cyclohexen-1-one → HCID 54051200, compound

HRID 2072272Notes

Reaction equation

HRID 2072272 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[CH:8]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1>ClCCl>[CH:3]12[CH2:4][CH2:5][CH2:6][C:1](=[O:7])[CH:2]1[CH:15]1[CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 135942-Cyclohexen-1-oneHCID 136091-Cyclooctene

Product 1

HCID 54051200HCID 54051200, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 29.4 g. (0.3 mol.) of cyclohexenone and 200 ml. of cyclooctene in 2600 ml. of dichloromethane was irradiated at -65° C. in the low temperature photolysis apparatus described in Organic Prep. Proc. Int. 3, 61 (1971) with a 1000 watt G.E. mercury arc through a Corning 9700 glass filter for 4 hours. At the end of the photolysis the solution was concentrated in vacuo and the product was distilled through a short Vigreux-column to yield 51.8 g. (0.249 mol., 83% yield) of a mixture of four isomers having b.p. 108°-127° C./0.4 mm.Hg. IR: 1695 cm-1 confirmed the structure.

Workup

  1. filtrationmercury arc through a Corning 9700 glass filter for 4 hours
  2. concentrationAt the end of the photolysis the solution was concentrated in vacuo
  3. distillationthe product was distilled through a short Vigreux-column
  4. customto yield 51.8 g
  5. addition(0.249 mol., 83% yield) of a mixture of four isomers

Sources & evidence

ORD record
ord-bda7e284fac94c0eb9f67219a1489cfd
Source dataset
uspto-grants-1977_09
Patent number
US04051076

Reaction notes

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