Acetone → 2-(6-Carboxy-2-cis-hexenyl)cyclopent-3-en-1-one

HRID 67016

Reaktionsgleichung

Reaktionsgleichung von HRID 67016
[OH:1][CH:2]1[CH2:6][CH:5]=[CH:4][CH:3]1/[CH:7]=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].CC(C)=O.[Cr](O)(O)(=O)=O>S(=O)(=O)(O)O>[C:13]([CH2:12][CH2:11][CH2:10][CH2:9]/[CH:8]=[CH:7]\[CH:3]1[CH:4]=[CH:5][CH2:6][C:2]1=[O:1])([OH:15])=[O:14]

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 24425Chromic AcidHCID 867329701-Hydroxy-2-(6-carboxy-2-cis-hexenyl)cyclopent-3-ene

Produkt 1

HCID 867329692-(6-Carboxy-2-cis-hexenyl)cyclopent-3-en-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A solution of 3.2 g. (0.5 mole) of 1-hydroxy-2-(6-carboxy-2-cis-hexenyl)cyclopent-3-ene (Example 1132) in 60 ml. of reagent acetone is treated dropwise with a total of 6 ml. of 8 N chromic acid in sulfuric acid at 0° C. The oxidation is rather slow. The resulting mixture is dissolved in 200 ml. of water and the solution is extracted with six 50 ml portions of ether. The combined ethereal extracts are dried over sodium sulfate and the solvent is evaporated at reduced pressure to yield the product as a yellow oil.

Aufarbeitung

  1. customat 0° C
  2. dissolutionThe resulting mixture is dissolved in 200 ml
  3. extractionof water and the solution is extracted with six 50 ml portions of ether
  4. dry with materialThe combined ethereal extracts are dried over sodium sulfate
  5. customthe solvent is evaporated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-13f5871605f04517a30b3a728b0bbfa8
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04343949

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