Water → HCID 21431778, compound

HRID 436929Notes

Reaction equation

HRID 436929 reaction equation
[CH:1]1([C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]#N)=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.[OH-:16].[K+].[OH2:18]>C(O)C>[CH:1]1([C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:18])=[O:16])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 21431782HCID 21431782, compound

Product 1

HCID 21431778HCID 21431778, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-(Cyclobutylcarbonyl)phenylacetonitrile (8.1 g) in ethanol (50 ml) was added to potassium hydroxide (6.8 g) in water (50 ml) and the mixture was heated under reflux for 5 hours and cooled. The solution was diluted with water (100 ml), washed with ether (2× 100 ml), acidified to pH 1 with hydrochloric acid and extracted with ether (3× 100 ml). The combined extracts were dried over magnesium sulphate, filtered and evaporated to give a brown oil. This was extracted with a hot mixture of light petroleum (b.p. 60°-80°) and ethyl acetate (9:1) (3× 200 ml). The solid that crystallised from the extracts on cooling was collected. It had m.p. 91°-92.5°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. temperaturecooled
  4. washwashed with ether (2× 100 ml)
  5. extractionextracted with ether (3× 100 ml)
  6. dry with materialThe combined extracts were dried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customto give a brown oil
  10. extractionThis was extracted with a hot mixture of light petroleum (b.p. 60°-80°) and ethyl acetate (9:1) (3× 200 ml)
  11. customThe solid that crystallised from the extracts
  12. temperatureon cooling
  13. customwas collected

Sources & evidence

ORD record
ord-e50ed423ae5c4accb59eca5cde5cc740
Source dataset
uspto-grants-1977_06
Patent number
US04028404

Reaction notes

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