Formaldehyde → Dimethyl itaconate

HRID 358824Notes

Reaction equation

HRID 358824 reaction equation
C=O.[CH:3]([CH:5]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[C:6]([O:8][CH3:9])=[O:7])=O>CO.C(O)(=O)C.CNC>[C:6]([O:8][CH3:9])(=[O:7])[C:5]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH2:3]

Participants

6

Reactant 2

HCID 712FormaldehydeHCID 93917Dimethyl formylsuccinate

Product 1

HCID 69240Dimethyl itaconateYield 96.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 674DimethylamineCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

60 g of paraformaldehyde are added to a solution of 6.0 g of acetic acid and 6.75 g of dimethylamine in 800 g of methanol, after which 348 g of dimethyl 2-formylsuccinate are added dropwise in the course of 20 minutes. The mixture is stirred for 7 hours at 50° C. and allowed to cool, and methanol and methyl formate are distilled off. The residue is taken up in ethyl acetate and the solution is washed with 100 g of 10% strength sulfuric acid and distilled. 305 g of isomer-free dimethyl itaconate of boiling point 42°-43° C. under 0.3-0.4 mbar are obtained, corresponding to a yield of 96.4% of theory.

Workup

  1. temperatureto cool
  2. distillationmethanol and methyl formate are distilled off
  3. washthe solution is washed with 100 g of 10% strength sulfuric acid
  4. distillationdistilled

Sources & evidence

ORD record
ord-1a062d7b7f2c47c1bdd10e685c9e82cf
Source dataset
uspto-grants-1991_03
Patent number
US04997955

Reaction notes

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