Methanol → 3-Furancarboxylic acid, 2,5-dimethyl-, methyl ester

HRID 1706336

Reaction equation

HRID 1706336 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.CO.ClC(Cl)C>[Fe].O>[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

7

Reactant 4

HCID 887MethanolHCID 63651,1-DichloroethaneHCID 7757Methyl acetoacetateHCID 907282-(Acetyloxy)propanal

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

12.2 parts by weight of anhydrous iron-III chloride followed by 44.9 parts by weight of 85.5 percent strength by weight α-acetoxypropionaldehyde are added to a solution of 34.8 parts by weight of methyl acetoacetate in 36 parts by weight of methanol, during which addition the mixture rises to the boil. The mixture is then refluxed for a further 1-6 hours and, when it has cooled, is mixed with 80 parts by weight of water and 37.5 parts by weight of dichloroethane; the water phase is separated off and is extracted twice, each time with 25 parts by weight of dichloroethane. The dichloroethane is distilled off under atmospheric pressure and the product is then distilled under reduced pressure. 39 parts by weight of 2,5-dimethylfuran-3-carboxylic acid methyl ester of boiling point 92° C./26 mbar are obtained.

Workup

  1. temperatureThe mixture is then refluxed for a further 1-6 hours
  2. temperaturewhen it has cooled
  3. customthe water phase is separated off
  4. extractionis extracted twice
  5. distillationThe dichloroethane is distilled off under atmospheric pressure
  6. distillationthe product is then distilled under reduced pressure

Sources & evidence

ORD record
ord-070831e44dd6489fbf0c38adfbe88d25
Source dataset
uspto-grants-1980_06
Patent number
US04207243

Linked notes

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