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

HRID 2301730Notes

Reaction equation

HRID 2301730 reaction equation
O[CH:2]([CH:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12])[CH2:3][CH2:4][CH2:5][CH3:6].Cl.[OH-].[Na+]>C(O)CCC>[CH2:2]([C:7]1[C:8](=[O:12])[CH2:9][CH2:10][CH:11]=1)[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 162060Cyclopentanone, 2-(1-hydroxypentyl)-

Product 1

HCID 1175492-Cyclopenten-1-one, 2-pentyl-Yield 60.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

42.6 g of 2-(1-hydroxypentyl)-cyclopentanone were dissolved in 161.9 g of n-butanol and heated to 130° C. Then, 24.5 g (0.24 mol) of a 35% hydrochloric acid were added dropwise thereto for 30 minutes at the same temperature. After the 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 8. As the result, 22.9 g of 2-pentyl-2-cyclopentenone were obtained (yield: 60.0%).

Workup

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

Sources & evidence

ORD record
ord-b0aeca26fb8141c3a5b7ee13f25d77a7
Source dataset
uspto-grants-2002_12
Patent number
US06500990B2

Reaction notes

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