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

HRID 1900393Notes

Reaction equation

HRID 1900393 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-0a4f1a28960c4077b7e450364de0ea19
Source dataset
uspto-grants-1996_11
Patent number
US05574032

Reaction notes

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