Hydrochloric Acid → 2,3-Dihydro-6-hydroxy-7-methoxy-5-benzofurancarboxaldehyde

HRID 2419544

Reaktionsgleichung

Reaktionsgleichung von HRID 2419544
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][C:4]=1[OH:12].Cl.C[CH2:15][O:16]CC>[C-]#N.[Zn+2].[C-]#N>[OH:12][C:4]1[C:5]([CH:15]=[O:16])=[CH:6][C:7]2[CH2:8][CH2:9][O:10][C:11]=2[C:3]=1[O:2][CH3:1]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 218565712,3-Dihydro-7-methoxy-6-benzofuranol

Produkt 1

HCID 218565722,3-Dihydro-6-hydroxy-7-methoxy-5-benzofurancarboxaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11186Zinc cyanide (Zn(CN)2)Katalysator

Versuchsvorschrift

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°.

Aufarbeitung

  1. additionA mixture of 2.49 g
  2. waitto stand overnight at room temperature
  3. concentrationthen concentrated in vacuo
  4. additionthe residue treated with 100 ml
  5. temperatureof 0.1N HCl for 1 hour at reflux
  6. temperatureAfter cooling
  7. extractionether extraction
  8. customprovided the product which
  9. customwas purified by chromatography over silica gel (E. Merck 60)
  10. washeluting with CHCl3
  11. customto yield a colorless solid, m.p. 71°-72°

Quellen und Nachweise

ORD-Eintrag
ord-c06526962ddc4d3d9083bee231100b09
Quelldatensatz
uspto-grants-1978_08
Patentnummer
US04107182

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