Sulfuric Acid → Dimedone

HRID 1759447Notes

Reaction equation

HRID 1759447 reaction equation
[O:1]=[C:2]([CH3:11])[CH2:3][C:4]([CH3:10])([CH3:9])[CH2:5][C:6](O)=[O:7].S(=O)(=O)(O)O>C(Cl)(Cl)Cl>[CH3:9][C:4]1([CH3:10])[CH2:3][C:2](=[O:1])[CH2:11][C:6](=[O:7])[CH2:5]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 113326103,3-Dimethyl-5-oxohexanoic acid

Product 1

HCID 31358DimedoneYield 82.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5 parts of 5-keto-3,3-dimethylhexanoic acid and about 15 parts of 73% sulfuric acid was heated for one hour in a 130°-135° oil bath. The cooled solution was then poured into a separatory funnel containing ice and chloroform. The aqueous phase was then washed three times with additional chloroform. The combined organic extractions were then dried and evaporated. There was obtained an 82.3% yield of dimedone. It was further recrystallized from toluene.

Workup

  1. additionThe cooled solution was then poured into a separatory funnel
  2. washThe aqueous phase was then washed three times with additional chloroform
  3. extractionThe combined organic extractions
  4. customwere then dried
  5. customevaporated

Sources & evidence

ORD record
ord-4f8baf3f340a49f9be3fac99b56f61fc
Source dataset
uspto-grants-1982_07
Patent number
US04340753

Reaction notes

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