Isophorone → HCID 54032451, compound

HRID 2072271Notes

Reaction equation

HRID 2072271 reaction equation
[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([CH3:10])=[CH:3]1.[CH:11]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1>ClCCl>[CH3:10][C:4]12[CH2:5][C:6]([CH3:8])([CH3:7])[CH2:9][C:2](=[O:1])[CH:3]1[CH:18]1[CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 6544IsophoroneHCID 136091-Cyclooctene

Product 1

HCID 54032451HCID 54032451, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 5-liter flask equipped with a quartz immersion well and nitrogen bubbler was added, under nitrogen, 138 g. (1.0 mol.) of isophorone and 420 g. of freshly distilled cyclooctene. The flask was filled with dichloromethane and was bubbled with nitrogen for 1 hour. The solution was irradiated for 18.5 hours with an Hanovia 450 watt medium pressure mercury arc through a Corning 9700 glass filter. After 7 hours, an additional 82 g. of cyclooctene was added. The solution was concentrated in vacuo to obtain an oil which was distilled through a 45 cm. Vigreux-column to yield 218.4 g. (0.881 mol., 88% yield) of product, b.p. 106°-110° C./0.3 mm.Hg. The product by glpc consisted of 3 isomers in the approximate ratio of 75:12.5:12.5. IR: 1692 cm-1 confirmed the production of the desired product.

Workup

  1. additionnitrogen bubbler was added, under nitrogen
  2. customwas bubbled with nitrogen for 1 hour
  3. customThe solution was irradiated for 18.5 hours with an Hanovia 450 watt medium pressure mercury arc through a Corning 9700 glass
  4. filtrationfilter
  5. additionof cyclooctene was added
  6. concentrationThe solution was concentrated in vacuo
  7. customto obtain an oil which
  8. distillationwas distilled through a 45 cm
  9. customVigreux-column to yield 218.4 g

Sources & evidence

ORD record
ord-4796565550c9411e840bd4b5950f4d04
Source dataset
uspto-grants-1977_09
Patent number
US04051076

Reaction notes

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