Malonic Acid → 93132-76-4

HRID 2227882Notes

Reaction equation

HRID 2227882 reaction equation
[CH3:1][C:2]1([CH3:11])[C@@H:4]([CH:5]=O)[C@@H:3]1[C:7]([O:9][CH3:10])=[O:8].[C:12](O)(=O)[CH2:13][C:14]([OH:16])=[O:15].CCCCCC>C(OCC)(=O)C>[CH3:1][C:2]1([CH3:11])[C@@H:4](/[CH:5]=[C:13](/[C:14]([OH:16])=[O:15])\[CH3:12])[C@@H:3]1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8058HexaneHCID 1302373541301-44-4

Product 1

HCID 644345793132-76-4

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Under a nitrogen atmosphere, 0.666 g of methyl (±)-trans-2,2-dimethyl-3-formylcyclopropanecarboxylate was dissolved in 10 mL of a designated solvent. A designated amount of an amine and 1.000 g of malonic acid was then added thereto, and the resulting mixture was stirred under heating. After the mixture was allowed to cool to room temperature, 50 mL of ethyl acetate was added to said mixture and the resulting mixture was washed with 3N-hydrochloric acid and then saturated brine to obtain an organic layer therefrom. The organic layer was dried over anhydrous magnesium sulfate and thereafter evaporated under reduced pressure in order to produce a residue. The residue was subjected to silica gel chromatography, wherein the eluent was a mixture of n-hexane and ethyl acetate at a volume to volume ratio of 3:1. Methyl(±)-trans-2,2-dimethyl-3-{2-carboxy-(E)-1-propenyl}cyclopropanecarboxylate was obtained.

Workup

  1. temperatureunder heating
  2. washthe resulting mixture was washed with 3N-hydrochloric acid
  3. customsaturated brine to obtain an organic layer
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure in order
  6. customto produce a residue

Sources & evidence

ORD record
ord-0dad18dc70b64489a620f0a078b15a51
Source dataset
uspto-grants-2002_07
Patent number
US06414181B1

Reaction notes

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