Реакция #54178

Уравнение реакции

2,3-dihydro-7-methoxy-6-benzofuranol

hydrogen chloride

ether

→

2,3-Dihydro-6-hydroxy-7-methoxy-5-benzofurancarboxaldehyde

Условия реакции

Обработка

1. 1
   workup.WAITto stand overnight at room temperature
2. 2
   Концентрированиеthen concentrated in vacuo
3. 3
   workup.ADDITIONthe residue treated with 100 ml
4. 4
   Температураof 0.1N HCl for 1 hour at reflux
5. 5
   ТемператураAfter cooling
6. 6
   Экстракцияether extraction
7. 7
   Другоеprovided the product which
8. 8
   Другоеwas purified by chromatography over silica gel (E. Merck 60)
9. 9
   Промывкаeluting with CHCl3
10. 10
    Другоеto yield a colorless solid, m.p. 71°-72°

Методика

A mixture of 2.49 g (15 mmole) of 2,3-dihydro-7-methoxy-6-benzofuranol, 5,87 g. (50 mmole) zinc cyanide and 100 ml. of dry ether was saturated with hydrogen chloride for 1 hour at 0°, then for 2 hours at room temperature. The mixture was then allowed to stand overnight at room temperature then concentrated in vacuo and the residue treated with 100 ml. of 0.1N HCl for 1 hour at reflux. After cooling, ether extraction provided the product which was purified by chromatography over silica gel (E. Merck 60), eluting with CHCl3, to yield a colorless solid, m.p. 71°-72°.

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