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

HRID 1706337

Reaction equation

HRID 1706337 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C(O[CH:13]([CH3:16])[CH:14]=O)(=O)C>[Fe].CO>[CH3:8][O:7][C:1]([C:2]1[CH:14]=[C:13]([CH3:16])[O:4][C:3]=1[CH3:5])=[O:6]

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

Conditions

Temperature
20 °C

Procedure

27 parts by weight of anhydrous iron-III chloride are added to a solution of 116 parts by weight of methyl acetoacetate in 120 parts by weight of methanol and thereafter 149 parts by weight of 85.5 percent strength α-acetoxypropionaldehyde are added dropwise, sufficiently slowly that the temperature does not rise above 37° C. The mixture is stirred overnight at room temperature (20° C.), is then boiled for 2 hours, and, when it has cooled, is worked up as described in Example 1. Distillation gives 116.6 parts by weight of 2,5-dimethylfuran-3-carboxylic acid methyl ester.

Workup

  1. customdoes not rise above 37° C
  2. waitis then boiled for 2 hours
  3. temperaturewhen it has cooled
  4. distillationDistillation

Sources & evidence

ORD record
ord-30828b858241423fa202fd29149a5bd0
Source dataset
uspto-grants-1980_06
Patent number
US04207243

Linked notes

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