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

HRID 1903987Notes

Reaction equation

HRID 1903987 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 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.

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-2cd45fa81e7b4aa2944ef04974baffa5
Source dataset
uspto-grants-1984_03
Patent number
US04439365

Reaction notes

Loading…