Ethanol → 2-(Butylsulfanyl)cyclopentan-1-one

HRID 851834

Reaction equation

HRID 851834 reaction equation
[Na].[CH2:2]([SH:6])[CH2:3][CH2:4][CH3:5].Cl[CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.C([OH:15])C>>[CH2:2]([S:6][CH:9]1[CH2:10][CH2:11][CH2:12][C:8]1=[O:15])[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 8012ButanethiolHCID 70252ChlorocyclopentaneHCID 5360545Sodium

Product 1

HCID 229313962-(Butylsulfanyl)cyclopentan-1-one

Procedure

Absolute ethanol (600 ml) was added with metal sodium (13.8 g) and butylmercaptan (64.8 g). A solution of 2-chlorocyclopentane (71.1 g) in absolute ethanol (600 ml) was added to the mixture and then was allowed to stand overnight at a low temperature. The ethanol was removed from the mixture, and the residue was dissolved in ether. The resulting solution was neutralized with aqueous acetic acid solution, the solvent was evaporated, and the resultant was then subjected to distillation, thereby giving 2-buthylthiocyclopentanone (90 g).

Workup

  1. customThe ethanol was removed from the mixture
  2. dissolutionthe residue was dissolved in ether
  3. customthe solvent was evaporated
  4. distillationthe resultant was then subjected to distillation
  5. customgiving 2-buthylthiocyclopentanone (90 g)

Sources & evidence

ORD record
ord-48e0187831ea4486b732e499f7c4ad21
Source dataset
uspto-grants-2007_08
Patent number
US07252849B2

Linked notes

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