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

HRID 2419544

반응식

HRID 2419544 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 11186Zinc cyanide (Zn(CN)2)촉매

실험 절차

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°.

후처리

  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°

출처 및 근거

ORD 기록
ord-c06526962ddc4d3d9083bee231100b09
출처 데이터셋
uspto-grants-1978_08
특허 번호
US04107182

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