Hydrochloric Acid → 1,3-Dicyclopropylpropane-1,3-dione

HRID 1455266Notes

Reaction equation

HRID 1455266 reaction equation
CO[C:3]([CH:5]1[CH2:7][CH2:6]1)=[O:4].[CH:8]1([C:11](=[O:13])[CH3:12])[CH2:10][CH2:9]1.C[O-].[Na+].Cl>CS(C)=O.C1(C)C=CC=CC=1>[CH:5]1([C:3](=[O:4])[CH2:12][C:11]([CH:8]2[CH2:10][CH2:9]2)=[O:13])[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13004Cyclopropyl methyl ketoneHCID 76122Methyl cyclopropanecarboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 137807821,3-Dicyclopropylpropane-1,3-dioneYield 78%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

Methylcyclopropanecarboxylate (20.2 ml, 286.3 mmol) was added to a stirred solution of 1-cyclopropylethanone (9 ml, 152.4 mmol) in dimethylsulfoxide (25 ml). Sodium methoxide powder (10.8 g, 200 mmol) was added, and the reaction was stirred at 55° C. for 8 hours. The reaction mixture was then cooled, diluted with toluene (200 ml), neutralised with 6M hydrochloric acid (50 ml), separated and then extracted with toluene (100 ml). The combined extracts were washed with sodium carbonate (150 ml), dried over magnesium sulphate and evaporated in vacuo to provide the title compound (14.9 g, 78%) as a mixture 2:1 enol:ketone forms.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customseparated
  3. extractionextracted with toluene (100 ml)
  4. washThe combined extracts were washed with sodium carbonate (150 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-da3d0511487c475db57e7ba596a57d61
Source dataset
uspto-grants-2009_01
Patent number
US07482375B2

Reaction notes

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