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

HRID 1706338

Reaction equation

HRID 1706338 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

27 parts by weight of iron-III chloride and 149 parts by weight of 85.5 percent strength α-acetoxypropionaldehyde are added to a solution of 116 parts by weight of methyl acetoacetate in 120 parts by weight of methanol at a rate such that the mixture rises to the boil. The methanol is distilled off under atmospheric pressure and the product is then distilled under reduced pressure. 106.2 parts by weight of 2,5-dimethylfuran-3-carboxylic acid methyl ester, of boiling point 89° C./20 mbar, are obtained.

Workup

  1. distillationThe methanol is distilled off under atmospheric pressure
  2. distillationthe product is then distilled under reduced pressure

Sources & evidence

ORD record
ord-c8642babbd0f4c62b60da3f1892d1dd2
Source dataset
uspto-grants-1980_06
Patent number
US04207243

Linked notes

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