Sodium Hydroxide → 2,5-Dimethyl-3-furoic acid

HRID 844275

Reaction equation

HRID 844275 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:12])=[CH:5][C:6]=1[C:7]([O:9]CC)=[O:8].[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[O:3][C:4]([CH3:12])=[CH:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1414573-Furancarboxylic acid, 2,5-dimethyl-, ethyl ester

Product 1

HCID 694652,5-Dimethyl-3-furoic acidYield 85.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.2 g of ethyl 2,5-dimethylfuran-3-carboxylate, 35 ml of ethanol and 20 ml of 2 N sodium hydroxide was stirred at room temperature for 1.5 hours followed by heating under reflux for an hour. After the reaction mixture was allowed to cool to room temperature, it was concentrated under reduced pressure. The residue was dissolved in water and acidified with diluted sulfuric acid. Precipitated crystals were collected by filtration, washed with water and dried to give 2.27 g of 2,5-dimethylfuran-3-carboxylic acid in a 85% yield.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for an hour
  3. temperatureto cool to room temperature
  4. concentrationit was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in water
  6. customPrecipitated crystals
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-e3a80f9624674176b0ed1b2286ce186f
Source dataset
uspto-grants-2002_04
Patent number
US06380247B2

Linked notes

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