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

HRID 2420431Notes

Reaction equation

HRID 2420431 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

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 8N 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.

Workup

  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
  4. dry with materialThe combined ethereal extracts are dried over sodium sulfate
  5. customthe solvent is evaporated at reduced pressure

Sources & evidence

ORD record
ord-6bb46565af294584b1651a99d37e65ae
Source dataset
uspto-grants-1978_08
Patent number
US04110368

Reaction notes

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