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

HRID 26373Notes

Reaction equation

HRID 26373 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

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

Procedure

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°.

Workup

  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°

Sources & evidence

ORD record
ord-976b891d71a945249f1df5c1e41ce565
Source dataset
uspto-grants-1979_04
Patent number
US04150042

Reaction notes

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