Bromine → 2-Hexyl-2-cyclopenten-1-one

Reaction equation

[CH:1](=[C:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].BrBr>>[CH2:1]([C:7]1[C:8](=[O:12])[CH2:9][CH2:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Reactant 2

HCID 24408Bromine

HCID 4574094Cyclopentanone, 2-hexylidene-

Product 1

HCID 667682-Hexyl-2-cyclopenten-1-oneYield 83.3%

Procedure

In a 50 ml three-neck flask fitted with a thermometer, a condenser and a stirrer were placed 2-hexylidenecyclopentanone (15 g) synthesized in Reference Example 5 and bromine (0.03 g), followed by 6 hours of the reaction at 100-120° C. The crude product was purified by column chromatography (hexane/ethyl acetate: 95/5) to obtain 12.5 g of 2-hexyl-2-cyclopentenone (GC purity: 98.5%).

Workup

customIn a 50 ml three-neck flask fitted with a thermometer, a condenser and a stirrer
customfollowed by 6 hours of the reaction at 100-120° C
customThe crude product was purified by column chromatography (hexane/ethyl acetate: 95/5)

Sources & evidence

ORD record: ord-6893ba2d4bad43319e96b1054b3f8c59
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06833481B2

Reaction notes

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