Sulfuric Acid → 5-Oxo-1-cyclopentene-1-heptanoic acid

HRID 426778

반응식

HRID 426778 반응식
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O.[OH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[C:28](=[O:32])[CH2:29][CH2:30][CH:31]=1>O.CC(C)=O.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[O-2].[O-2].[O-2].[Cr+6].[Cr]>[O:32]=[C:28]1[C:27]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:20]([OH:3])=[O:19])=[CH:31][CH2:30][CH2:29]1

참가 물질

9

반응물 3

HCID 1118Sulfuric AcidHCID 205354882-(7-Hydroxyheptyl)cyclopent-2-en-1-oneHCID 131709961Jones' reagent

생성물 1

HCID 789025-Oxo-1-cyclopentene-1-heptanoic acid

시약·촉매·용매 5

HCID 23976Chromium촉매HCID 10219390chromium (VI) trioxide촉매HCID 131709961Jones' reagent촉매HCID 180Acetone용매HCID 962Water용매3회

실험 절차

8N Jones reagent [90 ml; prepared by dissolving chromium trioxide (24.0 g) in a small volume of water, treating carefully with concentrated sulphuric acid (20.7 ml) and diluting with water to 90 ml with cooling] was added to a stirred solution of 2-(7-hydroxyheptyl)cyclopent-2-enone (39.2 g) in acetone (400 ml) at 10°-22° C. at a rate such that the deep red colouration caused by the addition of one drop of the Jones reagent had changed to green before addition of the next drop. The resulting mixture was then stirred at 15°-20° C. for 90 minutes. The reaction mixture was diluted with sufficient water to dissolve the precipitated chromium salts and was then extracted four times with diethyl ether. The combined ether extracts were washed with water, and then extracted three times with aqueous 2N sodium carbonate solution. The combined aqueous solutions were then acidified to pH 1 by the dropwise addition of concentrated hydrochloric acid and extracted twice with diethyl ether. The combined ethereal extracts were dried over magnesium sulphate and evaporated in vacuo to give an oil which crystallised on standing. Recrystallisation from a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether gave 7-(5-oxocyclopent-1-enyl)heptanoic acid (28 g), m.p. 41°-43° C.

후처리

  1. customprepared
  2. temperaturewith cooling]
  3. additiongreen before addition of the next drop
  4. extractionwas then extracted four times with diethyl ether
  5. washThe combined ether extracts were washed with water
  6. extractionextracted three times with aqueous 2N sodium carbonate solution
  7. additionThe combined aqueous solutions were then acidified to pH 1 by the dropwise addition of concentrated hydrochloric acid
  8. extractionextracted twice with diethyl ether
  9. dry with materialThe combined ethereal extracts were dried over magnesium sulphate
  10. customevaporated in vacuo
  11. customto give an oil which
  12. customcrystallised
  13. customRecrystallisation
  14. additionfrom a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether

출처 및 근거

ORD 기록
ord-54e7b69f1a384d3fa0723a82d8fbb06b
출처 데이터셋
uspto-grants-1979_10
특허 번호
US04171375

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