Potassium Cyanide → 5-(2-Cyano-5-oxocyclopentyl)pentyl acetate

HRID 2051784Notes

Reaction equation

HRID 2051784 reaction equation
[C-:1]#[N:2].[K+].[C:4]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[C:14](=[O:18])[CH2:15][CH2:16][CH:17]=1)(=[O:6])[CH3:5]>CO.C(O)(=O)C>[C:4]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[C:14](=[O:18])[CH2:15][CH2:16][CH:17]1[C:1]#[N:2])(=[O:6])[CH3:5]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 132897885-(5-Oxocyclopent-1-en-1-yl)pentyl acetate

Product 1

HCID 203783085-(2-Cyano-5-oxocyclopentyl)pentyl acetate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

98 g [1.5 mols] of potassium cyanide were suspended in 600 ml of methanol, and 105 g [0.5 mol] of 2-(5-acetoxypentyl)- cyclopent-2-ene-1-one, dissolved in 45 ml of acetic acid, were added dropwise within 2.5 hours. After 20 hours, agitation at room temperature, the suspension was dropped into ice-water with agitation, extracted thrice with diethyl ether, the ether phases were united, washed with water, dried over sodium sulfate and concentrated. The oily residue was stirred for 5 hours at room temperature in 200 ml of pyridine and 30 ml of acetic anhydride, the solvent was then distilled off under reduced pressure and the residue was distilled in a bulb tube. 102 g having a boiling point of 180° C. at 0.4 mm Hg were obtained; IR spectrum: 2220 cm-1.

Workup

  1. additionwere added dropwise within 2.5 hours
  2. extractionextracted thrice with diethyl ether
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. distillation30 ml of acetic anhydride, the solvent was then distilled off under reduced pressure
  7. distillationthe residue was distilled in a bulb tube
  8. customwere obtained

Sources & evidence

ORD record
ord-3fcd70aa684844a08e73ab3c27e6bbdf
Source dataset
uspto-grants-1980_01
Patent number
US04182773

Reaction notes

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