Acetone Cyanohydrin → 2-(7-Hydroxyheptyl)-3-oxocyclopentanecarbonitrile

HRID 1581090Notes

Reaction equation

HRID 1581090 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:10](=[O:14])[CH2:11][CH2:12][CH:13]=1.CC(C)(O)[C:17]#[N:18].C(=O)([O-])[O-].[Na+].[Na+]>CO>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[C:10](=[O:14])[CH2:11][CH2:12][CH:13]1[C:17]#[N:18]

Participants

5

Reactant 3

HCID 6406Acetone CyanohydrinHCID 10340Sodium CarbonateHCID 205354882-(7-Hydroxyheptyl)cyclopent-2-en-1-one

Product 1

HCID 205429242-(7-Hydroxyheptyl)-3-oxocyclopentanecarbonitrileYield 68.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(7-hydroxyheptyl)-2-cyclopenten-1-one (17 g., 0.087 mole), acetone cyanohydrin (8.5 g., 0.1 mole), 6% aqueous sodium carbonate (8 ml.) and methanol (50 ml.) was stirred and heated under reflux for 4 hours. Methanol was removed in vacuo, water (100 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-(7-hydroxyheptyl)-3-oxocyclopentanecarbonitrile (13.3 g., 68%), b.p. 144°-182°C./0.15 mm.Hg, nD25 1.4795.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. customMethanol was removed in vacuo, water (100 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-69a59cfe6d944a58af528e80a8ac5912
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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