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

HRID 976705Notes

Reaction equation

HRID 976705 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0bb62f162d3343ad8a9d78ebc3e16ea5
Source dataset
uspto-grants-1997_03
Patent number
US05612342

Reaction notes

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