Sodium Hydroxide → 2-Methyl-3-furoic acid

HRID 357782

Reaction equation

HRID 357782 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[CH:9][O:8][C:7]=1[CH3:11])=[O:5])C.[OH-].[Na+]>C(O)C>[CH3:11][C:7]1[O:8][CH:9]=[CH:10][C:6]=1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 261900Ethyl 2-Methyl-3-furoate

Product 1

HCID 2447562-Methyl-3-furoic acidYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methyl-3-furancarboxylic acid ethyl ester (10 g) was dissolved in ethanol (70 ml), and 1N aqueous sodium hydroxide (78 ml) was added. The mixture was stirred at room temperature and concentrated under reduced pressure. The residue was dissolved in water and washed with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Precipitated crystals were collected by filtration to give 2-methyl-3-furancarboxylic acid (5.5 g) as crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. washwashed with diethyl ether
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customPrecipitated crystals
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-b933f011bb044043b97cfc5f3657c2dd
Source dataset
uspto-grants-1998_11
Patent number
US05840917

Linked notes

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