香草乙酮 → (Z)-1-[4-[(4-chloro-2-butenyl)oxy]-3-methoxyphenyl]ethanone

HRID 233861

反应方程式

HRID 233861 反应方程式
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1)=[O:3].C([O-])([O-])=O.[K+].[K+].[Cl:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]Cl>C(#N)C>[Cl:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][C:6]=1[O:11][CH3:12]

参与物

5

反应物 3

HCID 2214香草乙酮HCID 11430碳酸钾HCID 6432115顺式-1,4-二氯-2-丁烯

产物 1

HCID 57454977(Z)-1-[4-[(4-chloro-2-butenyl)oxy]-3-methoxyphenyl]ethanone收率 106.8%

试剂、催化剂与溶剂 1

HCID 6342乙腈溶剂

实验过程

A stirred mixture of 4-hydroxy-3-methoxyacetophenone (16.6 g, 10 mmole), K2CO3 (14 g, 100 mmol) and cis-1,4-dichloro-2-butene (Aldrich, 15 g, 120 mmol) in acetonitrile (250 ml) was heated at reflux for 2.5 hours. The mixture was filtered and concentrated to an oil. Purification was by flash chromatography. The fractions containing the purest product were combined and concentrated to give white crystals, 7.7 g, 30%. This was recrystallized from ether to give analytical pure (Z)-1-[4-[(4-chloro-2-butenyl)oxy]-3-methoxyphenyl]ethanone (2.72 g), m.p.=64°-66° C.

后处理

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated to an oil
  5. customPurification
  6. additionThe fractions containing the purest product
  7. concentrationconcentrated
  8. customto give white crystals, 7.7 g, 30%
  9. customThis was recrystallized from ether

来源与证据

ORD记录
ord-fac6527b0e9f438783785bf2db2277cb
来源数据集
uspto-grants-1997_01
专利号
US05593995

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