Allyl bromide → 4-(allyloxy)-3-ethoxybenzaldehyde

HRID 746330Notes

Reaction equation

HRID 746330 reaction equation
[O:1]=[CH:2][C:3]1[CH:12]=[CH:11][C:9]([OH:10])=[C:5]([O:6][CH2:7][CH3:8])[CH:4]=1.[CH2:13](Br)[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:7]([O:6][C:5]1[CH:4]=[C:3]([CH:12]=[CH:11][C:9]=1[O:10][CH2:15][CH:14]=[CH2:13])[CH:2]=[O:1])[CH3:8]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8467EthylvanillinHCID 11430Potassium Carbonate

Product 1

HCID 35257364-(allyloxy)-3-ethoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl vanillin (21.6 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-90a5edfca4904f35b1b810a6754cd3bb
Source dataset
uspto-grants-2008_07
Patent number
US07393367B2

Reaction notes

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