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

HRID 1580250노트

반응식

HRID 1580250 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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 2 1/4 hours, a solution of 10.4 parts of dl- 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 dl- 3-hydroxy-5-oxo-2-styrylcyclopent-1-eneheptanoic 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.

후처리

  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

출처 및 근거

ORD 기록
ord-ad939e1687a94bf484620a96f631e540
출처 데이터셋
uspto-grants-1976_01
특허 번호
US03932467

반응 노트

불러오는 중…