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

HRID 259197

Reaction equation

HRID 259197 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 68.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(7-hydroxyheptyl)cyclopent-2-en-1-one (17 g.), acetone cyanohydrin (8.5 g.), 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 the extract 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.), 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 materialthe extract dried over magnesium sulphate
  7. customThe solvent was removed by evaporation
  8. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-5b33279ffd134d5c9b7ef43a94ef06cd
Source dataset
uspto-grants-1977_07
Patent number
US04036872

Linked notes

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