Ethanol → Cyclohex-2-ene-1,2-dicarboxylic acid

HRID 329559Notes

Reaction equation

HRID 329559 reaction equation
C([C:3]1[CH:4]([C:9]([O:11]CC)=[O:10])C[CH2:6][CH2:7][CH:8]=1)#N.[OH-:14].[K+].[CH2:16]([OH:18])[CH3:17]>>[CH:3]1[CH2:8][CH2:7][CH2:6][CH:17]([C:16]([OH:14])=[O:18])[C:4]=1[C:9]([OH:11])=[O:10]

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 15051955HCID 15051955, compound

Product 1

HCID 15051956Cyclohex-2-ene-1,2-dicarboxylic acid

Procedure

A stirred solution of 12.0 grams (0.067 mole) of ethyl 2-cyanocyclohex-2-enecarboxylate (prepared by the method of G. Kon and B. Nandi, JCS, 1628-1633 (1933), and 75 ml of aqueous 30% potassium hydroxide in approximately 20 ml of ethanol was heated under reflux for 16 hours. The reaction mixture was cooled and concentrated under reduced pressure to a residue. The residue was cooled in an ice bath, and the pH was adjusted to 2 with sulfuric acid. The resultant precipitate was collected by filtration and was dried to yield 5.0 grams of cyclohexene-2,3-dicarboxylic acid; m.p. 201°-203° C.

Workup

  1. temperatureunder reflux for 16 hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure to a residue
  4. temperatureThe residue was cooled in an ice bath
  5. filtrationThe resultant precipitate was collected by filtration
  6. customwas dried

Sources & evidence

ORD record
ord-11ce958ed2aa4adea2bf9e4574d9c76e
Source dataset
uspto-grants-1990_01
Patent number
US04892578

Reaction notes

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