Iodine → 2-Cyclopenten-1-one, 2-pentyl-

HRID 2308077Notes

Reaction equation

HRID 2308077 reaction equation
[CH:1](=[C:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])[CH2:2][CH2:3][CH2:4][CH3:5].II>>[CH2:1]([C:6]1[C:7](=[O:11])[CH2:8][CH2:9][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

3

Reactant 2

HCID 807IodineHCID 860002-Pentylidenecyclopentanone

Product 1

HCID 1175492-Cyclopenten-1-one, 2-pentyl-Yield 78%

Procedure

In a 100 ml four-neck flask fitted with a thermometer, a reflux condenser and a stirrer were placed 2-pentylidenecyclopentanone (50 g) synthesized in Reference Example 4 and iodine (5 mg), followed by 3 hours of the reaction at 180° C. The crude product (50 g) was distilled without any treatment using a Claisen distillation apparatus to obtain 39 g of 2-pentyl-2-cyclopentenone (boiling point: 105° C./933 Pa; GC purity: 98.3%).

Workup

  1. customIn a 100 ml four-neck flask fitted with a thermometer, a reflux condenser and a stirrer
  2. customfollowed by 3 hours of the reaction at 180° C
  3. distillationThe crude product (50 g) was distilled without any treatment
  4. distillationa Claisen distillation apparatus

Sources & evidence

ORD record
ord-205b044ec4cf4fcdaa34a7c80fb2488a
Source dataset
uspto-grants-2004_12
Patent number
US06833481B2

Reaction notes

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