Potassium Hydroxide → 3-Hydroxy-5-oxo-2-styrylcyclopent-1-eneheptanoic acid

HRID 1576405Notes

Reaction equation

HRID 1576405 reaction equation
[OH-].[K+].[C:3]1([CH:9]=[CH:10][C:11](=O)[CH:12]([OH:26])[CH2:13][C:14](=[O:25])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O.O.C(O)(=O)C(O)=O>C(Cl)(Cl)Cl>[OH:26][CH:12]1[CH2:13][C:14](=[O:25])[C:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[C:11]1[CH:10]=[CH:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 61373Oxalic acid dihydrateHCID 6813560614-Phenyl-9,12-dioxo-11-hydroxytetradec-13-enoic acid

Product 1

HCID 681356993-Hydroxy-5-oxo-2-styrylcyclopent-1-eneheptanoic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 3000 parts by volume of an aqueous solution containing 6.7 parts of potassium hydroxide is added, with stirring at 21°-23° over a period of about 21/4 hours, a solution of 10.4 parts of 14-phenyl-9,12-dioxo- 11-hydroxytetradec-13-enoic acid in 187 parts of chloroform. After completion of the addition, the reaction mixture is stirred for an additional 2 hours, then is made acidic by adding 10 parts of oxalic acid dihydrate. The acidic mixture is extracted with chloroform and the organic layer is washed with dilute aqueous sodium chloride, then dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure. The resulting residue is recrystallized first from benzene, then from chloroform-ether to yield 3-hydroxy-5-oxo-2 -styrylcyclopent-1eneheptanoic acid, which displays a melting point at about 118°. This compound displays an ultraviolet absorption maximum at about 325 millimicrons with a molecular extinction coefficient of about 36,400 and is further characterized by the following structural formula ##SPC3##

Workup

  1. additionis added
  2. additionAfter completion of the addition
  3. stirringthe reaction mixture is stirred for an additional 2 hours
  4. extractionThe acidic mixture is extracted with chloroform
  5. washthe organic layer is washed with dilute aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe resulting residue is recrystallized first from benzene

Sources & evidence

ORD record
ord-4284932ce3414e76bc9a107950517ff7
Source dataset
uspto-grants-1976_09
Patent number
US03980700

Reaction notes

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