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

HRID 970021Notes

Reaction equation

HRID 970021 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 mixture was cooled, diluted with toluene, neutralised with 6M hydrochloric acid, and then extracted with toluene. The combined extracts were washed with sodium carbonate, 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. 1H NMR (CDCl3, 400 MHz): δ=0.79-0.87 (m, 4H), 0.98-1.01 (m, 4H), 1.46-1.51 (m, 2H-enol), 1.93-1.97 (m, 2H-keto), 3.70 (s, 2H-keto), 5.65 (s, 1H-enol); LRMS: APCl+: m/z 153 [MH+]; APCl− m/z 151 [M−H]−.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with toluene
  3. washThe combined extracts were washed with sodium carbonate
  4. dry with materialdried over magnesium sulphate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-4e2cda04694c46cf9cb55f4415e30ff7
Source dataset
uspto-grants-2007_12
Patent number
US07309712B2

Reaction notes

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