1,2-Epoxybutane → 2(3H)-Furanone, 5-ethyldihydro-3-phenyl-

HRID 1703163Notes

Reaction equation

HRID 1703163 reaction equation
[CH2:1]([C:8]#N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:10].[K+].[O:12]1[CH:14]([CH2:15][CH3:16])[CH2:13]1>CN(C)C=O>[CH2:15]([CH:14]1[O:12][C:8](=[O:10])[CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13]1)[CH3:16]

Participants

5

Reactant 3

HCID 78341,2-EpoxybutaneHCID 8794PhenylacetonitrileHCID 14797Potassium Hydroxide

Product 1

HCID 122309672(3H)-Furanone, 5-ethyldihydro-3-phenyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 117 g. (1.0 m) benzyl cyanide, 72 g. (1.1 m) powdered 86% potassium hydroxide and 250 ml. dimethylformamide under a nitrogen atmosphere is added dropwise 74 g. (1.0 m) 1,2-epoxy-butane at 5° C. The temperature is held at 5° C. for 30 minutes and allowed to warm to room temperature. The reaction mixture is poured into 1,500 ml. water and extracted with 5×200 ml. toluene. To the combined toluene extracts is added 50 ml. of 50% hydrochloric acid and the mixture is heated on a steam bath for one hour. The toluene layer is then water washed until it is neutral, dried over sodium sulfate and filtered. The solvent is removed under vacuum to give 135 g. of a pale yellow oil.

Workup

  1. additionTo a mixture of 117 g
  2. customat 5° C
  3. additionThe reaction mixture is poured into 1,500 ml
  4. extractionwater and extracted with 5×200 ml
  5. additionTo the combined toluene extracts is added 50 ml
  6. temperatureof 50% hydrochloric acid and the mixture is heated on a steam bath for one hour
  7. washwater washed until it
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customThe solvent is removed under vacuum
  11. customto give 135 g

Sources & evidence

ORD record
ord-50bec738296c4badbebcb6322dbca3f2
Source dataset
uspto-grants-1982_09
Patent number
US04351839

Reaction notes

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