Acetovanillone → HCID 21960013, compound

HRID 2211529Notes

Reaction equation

HRID 2211529 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+].[Br:19][CH2:20][CH:21]=[CH:22][CH2:23]Br>CC(C)=O>[Br: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 131802-Butene, 1,4-dibromo-

Product 1

HCID 21960013HCID 21960013, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 4-hydroxy-3-methoxyacetophenone (10 g, 59 mmoles), K2CO3 (10 g, 1.2 q) and 1,4-dibromo-2-butene (>95% trans, Aldrich, 18 g, 1.2 eq) in acetone (500 ml) was heated at 55° C. for 3 hr. At the end of the reaction, the solvent was concentrated. The crude product was extracted into dichloromethane (750 ml) and the insolubles were filtered; then the solution was concentrated again to an oil. Purification on a silica gel column (SiO2, 100 g, eluted with dichloromethane) yielded 7.25 g (40%) of white solid. Recrystallization from ether gave analytically pure (E)-1-[4-[4-(4-bromo-2-butenyl)oxy]-3-methoxyphenyl]ethanone (3.91 g), m.p.=71°-72° C.

Workup

  1. customAt the end of the reaction
  2. concentrationthe solvent was concentrated
  3. extractionThe crude product was extracted into dichloromethane (750 ml)
  4. filtrationthe insolubles were filtered
  5. concentrationthen the solution was concentrated again to an oil
  6. customPurification
  7. washon a silica gel column (SiO2, 100 g, eluted with dichloromethane)

Sources & evidence

ORD record
ord-4fc87cd4de8946aca25e1a86d717d0e3
Source dataset
uspto-grants-2006_09
Patent number
USRE039265E1

Reaction notes

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