Methyl acetoacetate → 3-Furancarboxylic acid, 2,5-dimethyl-, methyl ester

HRID 1706339

Reaction equation

HRID 1706339 reaction equation
[C:1]([O:4][CH:5]([CH3:8])[CH:6]=O)(=O)[CH3:2].[C:9]([O:15][CH3:16])(=[O:14])[CH2:10]C(C)=O>[Fe].CO>[CH3:16][O:15][C:9]([C:10]1[CH:6]=[C:5]([CH3:8])[O:4][C:1]=1[CH3:2])=[O:14]

Participants

5

Reactant 2

HCID 7757Methyl acetoacetateHCID 907282-(Acetyloxy)propanal

Product 1

HCID 802483-Furancarboxylic acid, 2,5-dimethyl-, methyl ester

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

40 parts by weight of iron-III chloride and 136 parts by weight of 85 percent strength α-acetoxypropionaldehyde are added successively to a solution of 150 parts by weight of methyl acetoacetate in 120 parts by weight of methanol. The mixture, which becomes warm, is then refluxed for 2 hours. When it has cooled, the reaction solution is washed with water and distilled. 127 g of 2,5-dimethylfuran-3-carboxylic acid methyl ester are obtained.

Workup

  1. temperatureThe mixture, which becomes warm
  2. temperatureis then refluxed for 2 hours
  3. temperatureWhen it has cooled
  4. washthe reaction solution is washed with water
  5. distillationdistilled

Sources & evidence

ORD record
ord-a86d7762caed427391b66ee59855b844
Source dataset
uspto-grants-1980_06
Patent number
US04207243

Linked notes

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