Water → HCID 23499846, compound

HRID 436933Notes

Reaction equation

HRID 436933 reaction equation
[CH:1]1([C:4]([C:6]2[CH:7]=[C:8]([CH2:12][C:13]#N)[CH:9]=[CH:10][CH:11]=2)=[O:5])[CH2:3][CH2:2]1.[OH-:15].[K+].[OH2:17]>C(O)C>[CH:1]1([C:4]([C:6]2[CH:7]=[C:8]([CH2:12][C:13]([OH:17])=[O:15])[CH:9]=[CH:10][CH:11]=2)=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 21431785HCID 21431785, compound

Product 1

HCID 23499846HCID 23499846, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

m-(Cyclopropylcarbonyl)phenylacetonitrile (8.1 g) and potassium hydroxide (3.36 g) in water (50 ml) and ethanol (50 ml) were heated under reflux for 5 hours and cooled. The mixture was washed with chloroform (2× 50 ml), acidified to pH 1 with 5N hydrochloric acid and extracted with ethyl acetate (2× 75 ml). The extracts were combined, washed with water, dried over magnesium sulphate, filtered and evaporated. The residue was distilled under reduced pressure and the fraction b.p. 170°/0.1 mm collected. The distilate solidified and the solid melted at 52°.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperaturecooled
  3. washThe mixture was washed with chloroform (2× 50 ml)
  4. extractionextracted with ethyl acetate (2× 75 ml)
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. distillationThe residue was distilled under reduced pressure
  10. customthe fraction b.p. 170°/0.1 mm collected

Sources & evidence

ORD record
ord-7458c58b055e49bdb49a4de4dc85c3dd
Source dataset
uspto-grants-1977_06
Patent number
US04028404

Reaction notes

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