Ethanol → Nirvanol

HRID 2052392

Reaction equation

HRID 2052392 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=O)[CH2:2][CH3:3].[C:11](=[O:14])([O-])[O-].[NH4+:15].[NH4+:16].[C-]#N.[K+].[CH2:20]([OH:22])C>O>[CH2:2]([C:1]1([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:16][C:20](=[O:22])[NH:15][C:11]1=[O:14])[CH3:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 71481-Phenyl-1-propanoneHCID 9032Potassium CyanideHCID 517111Ammonium Carbonate

Product 1

HCID 91480NirvanolYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 26.8 g (0.2 mol) of propiophenone, 80 g (0.8 mol) of ammonium carbonate dissolved in 300 ml of water and 28 g (0.4 mol) of potassium cyanide in 300 ml of ethanol is heated under reflux for 8 hours, whilst stirring. The solution is cooled in a mixture of ice and salt; the hydantoin precipitates. The precipitate thus obtained is filtered off and washed with water. 27.1 g (yield: 66%) of 5-ethyl-5-phenyl-hydantoin, melting at 202° C., are obtained.

Workup

  1. temperatureunder reflux for 8 hours
  2. temperatureThe solution is cooled in a mixture of ice and salt
  3. customthe hydantoin precipitates
  4. customThe precipitate thus obtained
  5. filtrationis filtered off
  6. washwashed with water

Sources & evidence

ORD record
ord-4885bc7fa1ed4a74a57943cf14a82e64
Source dataset
uspto-grants-1980_01
Patent number
US04183951

Linked notes

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