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

HRID 266976

反応式

HRID 266976 の反応式
[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]

参加物

5

反応物 3

HCID 2214AcetovanilloneHCID 11430Potassium CarbonateHCID 64321151,4-Dichloro-cis-2-butene

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cca2b118b36b4153bbde8642c2edd950
出典データセット
uspto-grants-1997_07
特許番号
US05652241

関連ノート

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