Reaktion #341168

Reaktionsgleichung

ethyl 2-(furan-2-yl)-2-hydroxyacetate

trimethylorthoacetate

hexanoic acid

NaOH

→

2,3-di(carboxymethyl)furan

Lösungsmittel

decalin

methanol

decalin

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction is cooled
2. 2
   Extraktionextracted with methanol
3. 3
   Sonstigeto provide
4. 4
   SonstigeThe methanol is removed
5. 5
   Sonstigethe crude reaction
6. 6
   Extraktionis extracted with ether
7. 7
   Extraktionextracted with ethyl acetate
8. 8
   WaschenThe organic layer is washed with brine
9. 9
   Sonstigedried
10. 10
    Einengenconcentrated

Vorschrift

A solution of ethyl 2-(furan-2-yl)-2-hydroxyacetate (11.05 g, 64.5 mmol), trimethylorthoacetate (29.8 mL, 387 mmol) and hexanoic acid (2 mL) in decalin (195 mL) is heated at 180° C. for 12 hours. The reaction is cooled and extracted with methanol to provide a mixture of diester and decalin. This mixture is dissolved in methanol (250 mL), cooled to 0° C., treated with 2 M NaOH (150 mL) and stirred for 12 hours. The methanol is removed and the crude reaction is extracted with ether, and the basic layer is acidified with 6 N HCl and extracted with ethyl acetate. The organic layer is washed with brine, dried and concentrated to give 2,3-di(carboxymethyl)furan.

Quelle