Acetic Acid → HCID 21431780, compound

HRID 436934Notes

Reaction equation

HRID 436934 reaction equation
[CH2:1]1[CH2:6][CH2:5][CH:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2C(C#N)(C)C(OCC)=O)=[O:8])[CH2:3][CH2:2]1.S(=O)(=O)(O)O.O.[C:30]([OH:33])(=[O:32])[CH3:31].[CH3:34]COCC>>[CH:4]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH:31]([CH3:34])[C:30]([OH:33])=[O:32])=[CH:11][CH:10]=2)=[O:8])[CH2:5][CH2:6][CH2:1][CH2:2][CH2:3]1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962Water2×HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 131710811HCID 131710811, compound

Product 1

HCID 21431780HCID 21431780, compound

Procedure

2-(p-Cyclohexylcarbonyl)phenyl-2-cyanopropionic acid, ethyl ester (2.55 g, crude) was added to a mixture of concentrated sulphuric acid (5 ml), water (5 ml) and glacial acetic acid (17 ml) and the mixture was heated under reflux for 22 hours and cooled. Water (35 ml) was added and the mixture was shaken with ether (2× 50 ml). The ether solution was extracted with 2N sodium hydroxide (3× 50 ml) and the alkaline extract was acidified to pH2 with 5N hydrochloric acid. The acidic mixture was extracted with ether (2× 75 ml) and the extracts were dried over magnesium sulphate, filtered and evaporated to yield a brown oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 22 hours
  3. temperaturecooled
  4. extractionThe ether solution was extracted with 2N sodium hydroxide (3× 50 ml)
  5. extractionthe alkaline extract
  6. extractionThe acidic mixture was extracted with ether (2× 75 ml)
  7. dry with materialthe extracts were dried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customto yield a brown oil

Sources & evidence

ORD record
ord-65a42ce948304d1f87b8d4b820b5ffb4
Source dataset
uspto-grants-1977_06
Patent number
US04028404

Reaction notes

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