Ethyl Propionate → 1-Phenyl-2-butanone

HRID 1979499Notes

Reaction equation

HRID 1979499 reaction equation
[Na].[CH2:2](C#N)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:11]([O:15]CC)(=O)[CH2:12][CH3:13]>>[CH2:2]([C:11]([CH2:12][CH3:13])=[O:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 7749Ethyl PropionateHCID 8794PhenylacetonitrileHCID 5360545Sodium

Product 1

HCID 138791-Phenyl-2-butanoneYield 53.3%

Procedure

In a 2-liter flask provided with a thermometer, stirrer, dropping funnel and reflux condenser 600 ml of absolute alcohol are treated portionwise while stirring with 30 g of sodium metal and the mixture is held at reflux temperature until the metal has dissolved. Within 0.5 hour there is added dropwise to the boiling solution a mixture of 117.2 g of benzyl cyanide and 153.2 g of ethyl propionate and the mixture is heated for a further 3 hours. The alcohol is then distilled off and there are added 300 ml of toluene, followed by 250 ml of ice/water. The aqueous phase is separated, washed with 300 ml of toluene and then 540 g of 96% sulphuric acid are added. The mixture is held at reflux temperature until the evolution of carbon dioxide ceases, cooled, diluted with 250 ml of ice/water and extracted with two 300 ml portions of toluene. The toluene extracts are washed with water, with 10% sodium carbonate solution and again with water, dried over sodium sulphate and evaporated. Distillation gives 79 g of ethyl benzyl ketone of boiling point 69° C./3 mmHg; nD20 =1.5109; yield 53%.

Workup

  1. customIn a 2-liter flask provided with a thermometer, stirrer
  2. additionare treated portionwise
  3. temperatureat reflux temperature until the metal
  4. dissolutionhas dissolved
  5. additionWithin 0.5 hour there is added dropwise to the boiling solution
  6. temperaturethe mixture is heated for a further 3 hours
  7. distillationThe alcohol is then distilled off
  8. additionthere are added 300 ml of toluene
  9. customThe aqueous phase is separated
  10. washwashed with 300 ml of toluene
  11. addition540 g of 96% sulphuric acid are added
  12. temperatureat reflux temperature until the evolution of carbon dioxide ceases
  13. temperaturecooled
  14. additiondiluted with 250 ml of ice/water
  15. extractionextracted with two 300 ml portions of toluene
  16. washThe toluene extracts are washed with water, with 10% sodium carbonate solution and again with water
  17. dry with materialdried over sodium sulphate
  18. customevaporated
  19. distillationDistillation

Sources & evidence

ORD record
ord-883d54c20515486a8b8ddb22480bde97
Source dataset
uspto-grants-1984_11
Patent number
US04481133

Reaction notes

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