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

HRID 2301727Notes

Reaction equation

HRID 2301727 reaction equation
N1C=CC=C(C)C=1.Cl.C(O)CCCCC.[CH:16](=[C:21]1[CH2:25][CH2:24][CH2:23][C:22]1=[O:26])[CH2:17][CH2:18][CH2:19][CH3:20].[OH-].[Na+]>>[CH2:16]([C:21]1[C:22](=[O:26])[CH2:23][CH2:24][CH:25]=1)[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 5

HCID 313Hydrochloric Acid3×HCID 79703-MethylpyridineHCID 81031-HexanolHCID 14798Sodium HydroxideHCID 860002-Pentylidenecyclopentanone

Product 1

HCID 1175492-Cyclopenten-1-one, 2-pentyl-Yield 90.2%

Conditions

Temperature
160 °C

Procedure

15.09 g (0.16 mol) of 3-picoline and 5.63 g (0.055 mol) of a 35% hydrochloric acid were mixed with 82.2 g of n-hexanol and heated to 160° C. Then, 164.4 g (1.08 mol) of 2-pentylidene cyclopentanone were added dropwise thereto at the same temperature for 2 hours and a 35% hydrochloric acid was simultaneously added dropwise thereto at the rate of 1.41 g (0.014 mol)/h for 2 hours. After the dropping addition was finished, the resultant mixture was stirred for 5 hours under heating at the same temperature while the 35% hydrochloric acid was continuously added dropwise. 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, 148.3 g of 2-pentyl-2-cyclopentenone were obtained (yield: 90.2%).

Workup

  1. waitat the rate of 1.41 g (0.014 mol)/h for 2 hours
  2. additionAfter the dropping addition
  3. additionwas continuously added dropwise
  4. temperaturethe mixture was cooled to the room temperature

Sources & evidence

ORD record
ord-b4e22112dc9349d09673c90f793eb952
Source dataset
uspto-grants-2002_12
Patent number
US06500990B2

Reaction notes

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