Acetoin → 2,4,5-Trimethylfuran-3-carboxylic acid

HRID 972953Notes

Reaction equation

HRID 972953 reaction equation
O[CH:2]([CH3:6])[C:3](=[O:5])[CH3:4].[C:7]([O:13]CC)(=[O:12])[CH2:8][C:9]([CH3:11])=O.C(O)C>[Cl-].[Zn+2].[Cl-].O>[CH3:11][C:9]1[O:5][C:3]([CH3:4])=[C:2]([CH3:6])[C:8]=1[C:7]([OH:13])=[O:12]

Participants

6

Reactant 3

HCID 179AcetoinHCID 702EthanolHCID 8868Ethyl Acetoacetate

Product 1

HCID 71315072,4,5-Trimethylfuran-3-carboxylic acidYield 96%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-hydroxy-2-butanone (90g.) ethyl acetoacetate (175g.), absolute ethanol (150 ml.) and anhydrous zinc chloride (100g.) was heated under reflux for 24 hours. The cooled solution was poured into water and extracted with benzene. The benzene extract was washed successively with 30% aqueous sodium bisulfite, 5% sodium hydroxide, dilute hydrochloric acid and finally with water. The solvent was removed and the residual ester saponified with aqueous-alcoholic alkali as in example 18 to yield 149 g. or 96% yield of the 2,4,5-trimethyl-3-furoic acid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. extractionextracted with benzene
  4. extractionThe benzene extract
  5. washwas washed successively with 30% aqueous sodium bisulfite, 5% sodium hydroxide, dilute hydrochloric acid and finally with water
  6. customThe solvent was removed
  7. customto yield 149 g

Sources & evidence

ORD record
ord-5378fe5243864ca0923dc38af59786db
Source dataset
uspto-grants-1977_10
Patent number
US04054585

Reaction notes

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