Reaktion #57692

Reaktionsgleichung

4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

acetyl chloride

→

5-acetyl-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Ausbeute 59.0%

Lösungsmittel

chlorobenzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was sealed in a pressure tube
2. 2
   Sonstigewas placed in 95° C.
3. 3
   Sonstigefor 5 h
4. 4
   WaschenThe reaction mixture was washed with 0.5N HCl
5. 5
   Extraktionwas extracted with ethyl acetate
6. 6
   SonstigeRemoval of the solvents
7. 7
   Sonstigegave the crude product, which
8. 8
   Sonstigewas purified by column chromatography

Vorschrift

To 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester 0.5 g (2.27 mmol) was added 15 mL of chlorobenzene, 0.27 g (3.4 mmol) of acetyl chloride and 0.63 mL (5.7 mmol) of titanium tetrachloride. The mixture was sealed in a pressure tube and the tube was placed in 95° C. oil bath for 5 h with stirring. The reaction mixture was washed with 0.5N HCl and was extracted with ethyl acetate. Removal of the solvents gave the crude product, which was purified by column chromatography to give 0.33 g (59% yield) of 5-acetyl-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester as a white solid.

Quelle