Hydrogen Cyanide → Cyclohexanone cyanohydrin

HRID 1283569Notes

Reaction equation

HRID 1283569 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH:7]#[N:8].[C:9]1(=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>O>[CH2:12]1[CH2:13][CH2:14][C:9]([OH:15])([C:7]#[N:8])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 768Hydrogen CyanideHCID 7967CyclohexanoneHCID 10340Sodium Carbonate

Product 1

HCID 13610Cyclohexanone cyanohydrin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

Sodium carbonate (30.0 g., 0.283 mole) was dissolved in 200.2 g. of water, the system was closed and anhydrous liquid HCN (3.46 g., 0.128 mole) was added to the solution. Little, if any, heat was given off in the reaction and the product solution was clear. Cyclohexanone (32.05 g., 0.327 mole) was injected into the system with good mixing. The mixture heated up immediately 10°C. The organic and aqueous phases were mixed for 15 minutes longer and then allowed to separate. The organic layer (35.9 g.) was analyzed for free HCN, showing none, followed by an analysis for both combined and free HCN which showed 3.19 g. (0.118 mole) or 92% of the original HCN injected appearing in the organic phase as cyanohydrin.

Workup

  1. temperatureLittle, if any, heat
  2. customwas given off in the reaction
  3. additionThe organic and aqueous phases were mixed for 15 minutes longer
  4. customto separate

Sources & evidence

ORD record
ord-e9d84a458f50451cb4f08c0dd756f7c9
Source dataset
uspto-grants-1976_08
Patent number
US03975502

Reaction notes

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