Vanillin → 4-(allyloxy)-3-methoxybenzaldehyde

HRID 746328Notes

Reaction equation

HRID 746328 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[CH2:12](Br)[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:7][O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:8]=1[O:9][CH2:14][CH:13]=[CH2:12])[CH:2]=[O:1]

Participants

5

Reactant 3

HCID 1183VanillinHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 20638234-(allyloxy)-3-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Vanillin (20.0 g, 0.130 mol) and allyl bromide (19.9 g, 0.160 mol) were heated under reflux together with potassium carbonate (27.3 g, 0.200 mol) in 150 ml acetone (abs.) for 8 hours. After cooling, the solid was filtered off and washed with acetone. A yellow oil was obtained after a thorough concentration of the organic phases.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid was filtered off
  3. washwashed with acetone
  4. customA yellow oil was obtained
  5. concentrationafter a thorough concentration of the organic phases

Sources & evidence

ORD record
ord-2262e4da654c4dfa925ae01a12cfcfdc
Source dataset
uspto-grants-2008_07
Patent number
US07393367B2

Reaction notes

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