Acetone Cyanohydrin → HCID 20354863, compound

HRID 372124Notes

Reaction equation

HRID 372124 reaction equation
C([O:4][CH:5]1[C:9](=[O:10])[C:8]([CH2:11][CH2:12][CH:13]([O:19][C:20](=[O:22])[CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:7][CH2:6]1)(=O)C.CC(C)(O)[C:25]#[N:26].C(=O)([O-])[O-].[Na+].[Na+]>CO>[C:20]([O:19][CH:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:12][CH2:11][CH:8]1[CH:7]([C:25]#[N:26])[CH2:6][CH:5]([OH:4])[C:9]1=[O:10])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 6406Acetone CyanohydrinHCID 10340Sodium CarbonateHCID 20354859HCID 20354859, compound

Product 1

HCID 20354863HCID 20354863, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Acetoxy-2-(3-acetoxyoctyl)cyclopent-2-enone (15.5 g.) [prepared as described in (h) above], acetone cyanohydrin (6.0 g.), aqueous sodium carbonate solution (10.0% w/v; 5 ml.) and methanol (75 ml.) were stirred together and heated at reflux for 4 hours. Methanol was removed in vacuo, water (50 ml.) was added and the mixture extracted with diethyl ether. The ethereal extract was washed with water, dried with magnesium sulphate and evaporated in vacuo to give 2-(3-acetoxyoctyl)-3-cyano-5-hydroxycyclopentanone (14.3 g.) which was used as starting material in the following preparation (k) of 3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentane carbonitrile without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. customMethanol was removed in vacuo, water (50 ml.)
  4. additionwas added
  5. extractionthe mixture extracted with diethyl ether
  6. extractionThe ethereal extract
  7. washwas washed with water
  8. dry with materialdried with magnesium sulphate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-d3b1fe7c83d34a94b91a9bba46f1148f
Source dataset
uspto-grants-1978_05
Patent number
US04088821

Reaction notes

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