3-Cyclohexene-1-carboxaldehyde → 2-(3-Cyclohexen-1-yl)-2-hydroxyacetonitrile

HRID 1388116Notes

Reaction equation

HRID 1388116 reaction equation
[CH:1]1([CH:7]=[O:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.S(=O)(O)[O-].[Na+].[C-:14]#[N:15].[K+]>O>[CH:1]1([CH:7]([OH:8])[C:14]#[N:15])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

5

Reactant 3

HCID 75083-Cyclohexene-1-carboxaldehydeHCID 9032Potassium Cyanide2×HCID 23665763Sodium Bisulfite

Product 1

HCID 142936342-(3-Cyclohexen-1-yl)-2-hydroxyacetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

3-Cyclohexene-1-carbaldehyde (11.7 ml. 0.1 mole) and sodium bisulfite (15.5 g., 0.15 mole) were combined with 150 ml. of H2O and heated at 50°-60° C. for 2 hours. The mixture was cooled to 5° C. and added dropwise over 10 minutes to a cold solution of KCN (19.5 g., 0.3 mole) in 50 ml. H2O. The mixture was warmed to 20° C., KCN (6.5 g., 0.1 mole) added as a solid, stirred for 10 minutes, and product extracted into 100 ml. ethyl acetate. The ethyl acetate extract was washed with brine and evaporated to yield title product as an oil, 8.5 g., Rf (5:1 hexane:ethyl acetate/5% CH3CO2H) 0.5.

Workup

  1. temperatureThe mixture was warmed to 20° C.
  2. extractionproduct extracted into 100 ml
  3. extractionThe ethyl acetate extract
  4. washwas washed with brine
  5. customevaporated

Sources & evidence

ORD record
ord-d1319114f65b452d821aa077b2000bd2
Source dataset
uspto-grants-1984_02
Patent number
US04430337

Reaction notes

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