Iodine → 2-Hexyl-2-cyclopenten-1-one

HRID 2308073Notes

Reaction equation

HRID 2308073 reaction equation
O[CH:2]([CH:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].II>>[CH2:2]([C:8]1[C:9](=[O:13])[CH2:10][CH2:11][CH:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

3

Reactant 2

HCID 807IodineHCID 121355652-(1-Hydroxyhexyl)cyclopentanone

Product 1

HCID 667682-Hexyl-2-cyclopenten-1-oneYield 84.8%

Procedure

In a 30 ml four-neck flask fitted with a thermometer, a reflux condenser and a stirrer were placed 2-(1-hydroxyhexyl)cyclopentanone (20 g) synthesized in Reference Example 2 and iodine (5 mg), followed by 6 hours of the reaction at 150° C. The crude product was purified by column chromatography (hexane/ethyl acetate: 95/5) to obtain 15.3 g of 2-hexyl-2-cyclopentenone (GC purity: 99.1%).

Workup

  1. customIn a 30 ml four-neck flask fitted with a thermometer, a reflux condenser and a stirrer
  2. customfollowed by 6 hours of the reaction at 150° C
  3. customThe crude product was purified by column chromatography (hexane/ethyl acetate: 95/5)

Sources & evidence

ORD record
ord-239a2ccbc12c44468312bd39ee97ea12
Source dataset
uspto-grants-2004_12
Patent number
US06833481B2

Reaction notes

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