Hydrochloric Acid → 2-Cyclopenten-1-one, 2-pentyl-

HRID 2301728Notes

Reaction equation

HRID 2301728 reaction equation
N1C=CC=C(C)C=1.Cl.C(C(CCCC)CO)C.[CH:18](=[C:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28])[CH2:19][CH2:20][CH2:21][CH3:22].[OH-].[Na+]>>[CH2:18]([C:23]1[C:24](=[O:28])[CH2:25][CH2:26][CH:27]=1)[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 77202-EthylhexanolHCID 79703-MethylpyridineHCID 14798Sodium HydroxideHCID 860002-Pentylidenecyclopentanone

Product 1

HCID 1175492-Cyclopenten-1-one, 2-pentyl-Yield 86%

Conditions

Temperature
140 °C

Procedure

5.44 g (0.058 mol) of 3-picoline and 5.54 g (0.053 mol) of a 35% hydrochloric acid were mixed with 100.0 g of 2-ethylhexanol and heated to 140° C. Then, 100.0 g (0.53 mol) of 2-pentylidene cyclopentanone were added dropwise thereto for 2 hours at the same temperature. After this dropping addition was finished, the resultant mixture was stirred for 2 hours under heating at the same temperature. After the reaction was finished, the mixture was cooled to the room temperature and neutralized with an aqueous solution of sodium hydroxide. Then, the resultant organic layer was analyzed in the same manner as in Example 1. As the result, 69.2 g of 2-pentyl-2-cyclopentenone were obtained (yield: 86.0%).

Workup

  1. additionAfter this dropping addition
  2. temperatureunder heating at the same temperature
  3. temperaturethe mixture was cooled to the room temperature

Sources & evidence

ORD record
ord-3d4322aa77d944a28a940207b3800627
Source dataset
uspto-grants-2002_12
Patent number
US06500990B2

Reaction notes

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