Methanol → Methyl thiophen-2-acetate

Reaktionsgleichung

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([OH:9])=[O:8].OS(O)(=O)=O.[CH3:15]O>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([O:9][CH3:15])=[O:8]

Komponenten

Edukt 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 159702-Thiopheneacetic acid

Produkt 1

HCID 88055Methyl thiophen-2-acetateAusbeute 91 %

Versuchsvorschrift

Thiophene acetic acid (27.3 g, 192 mmol) was treated with a solution of H2SO4 (5.76 mL, 108 mmol) in MeOH (384 mL) at reflux for one hour. The reaction was then cooled to room temperature, concentrated by rotovap, diluted with ether, washed with 5% sodium bicarbonate and brine. The organic phase was then dried with magnesium sulfate and concentrated by rotovap to yield the product as a yellow oil (27.4 g, 176 mmol, 91%), which was used without further purification. The product matches data for commercially available methyl 2-(thiophen-2-yl)acetate (CAS No. 19432-68-9).