Acetone Cyanohydrin → 2-(6-Hydroxyhexyl)-3-oxocyclopentane-1-carbonitrile

HRID 1581101Notes

Reaction equation

HRID 1581101 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[C:9](=[O:13])[CH2:10][CH2:11][CH:12]=1.CC(C)(O)[C:16]#[N:17].C(=O)([O-])[O-].[Na+].[Na+]>CO>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[C:9](=[O:13])[CH2:10][CH2:11][CH:12]1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 6406Acetone CyanohydrinHCID 10340Sodium CarbonateHCID 215614872-(6-Hydroxyhexyl)-2-cyclopenten-1-one

Product 1

HCID 215615032-(6-Hydroxyhexyl)-3-oxocyclopentane-1-carbonitrileYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(6-hydroxyhexyl)-2-cyclopenten-1-one (10.5 g., 0.058 mole), acetone cyanohydrin (5.6 g., 0.065 mole), 6% aqueous sodium carbonate (5.2 ml.) and methanol (35 ml.) was stirred and heated under reflux for 4 hours. Methanol was removed in vacuo, water (70 ml.) was added and the mixture was extracted with diethyl ether and dried over magnesium sulphate. The solvent was removed by evaporation and the residue was distilled under reduced pressure to give 2-(6-hydroxyhexyl)-3-oxocyclopentanecarbonitrile (8.8 g., 73%), b.p. 135°-178°C./0.15 mm.Hg, nD25 1.4812.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. customMethanol was removed in vacuo, water (70 ml.)
  4. additionwas added
  5. extractionthe mixture was extracted with diethyl ether
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was removed by evaporation
  8. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-0e813889be024d96b63531a18beb2ad3
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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