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

HRID 372045

Reaktionsgleichung

Reaktionsgleichung von HRID 372045
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 205429242-(7-Hydroxyheptyl)-3-oxocyclopentanecarbonitrileAusbeute 68,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-93242c09198e4e669d88a20c53787e0c
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04088695

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