Potassium Hydroxide → cyclohex-2-en-1-ylacetic acid

HRID 543516Notes

Reaction equation

HRID 543516 reaction equation
C([O:3][C:4](=[O:17])[CH:5]([CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]=[CH:12]1)C(OCC)=O)C.[OH-].[K+]>O.CO>[CH:11]1([CH2:5][C:4]([OH:17])=[O:3])[CH2:16][CH2:15][CH2:14][CH:13]=[CH:12]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 237534Diethyl (cyclohex-2-en-1-yl)propanedioate

Product 1

HCID 227350cyclohex-2-en-1-ylacetic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

100 g of 2-(2-cyclohexenyl)malonic acid diethyl ester and 52 g of potassium hydroxide in 100 ml of water/methanol=1/4 was refluxed overnight. Then the alcohol was withdrawn on a forced circulation evaporator, the residue was diluted with about 200 ml of water and then combined under ice cooling with about 70 ml of concentrated hydrochloric acid to pH 1. The mixture was repeatedly extracted with ether, the combined organic phases were washed with saturated sodium chloride solution and evaporated to dryness. The residue was heated for 4 hours to 130° C. with liberation of CO2 and thereafter distilled under vacuum, thus obtaining 55.5 g, bp1 98°-107° C.

Workup

  1. customThen the alcohol was withdrawn on a forced circulation evaporator
  2. additionthe residue was diluted with about 200 ml of water
  3. extractionThe mixture was repeatedly extracted with ether
  4. washthe combined organic phases were washed with saturated sodium chloride solution
  5. customevaporated to dryness
  6. temperatureThe residue was heated for 4 hours to 130° C. with liberation of CO2
  7. distillationdistilled under vacuum
  8. customthus obtaining 55.5 g, bp1 98°-107° C.

Sources & evidence

ORD record
ord-e201d24ac2ab4283abe2e2f9f5f1f5c8
Source dataset
uspto-grants-1984_05
Patent number
US04446147

Reaction notes

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