Allyl bromide → 3-Allyloxy-4-methoxybenzaldehyde

HRID 1493429Notes

Reaction equation

HRID 1493429 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.[CH2:12](Br)[CH:13]=[CH2:14]>C(=O)([O-])[O-].[K+].[K+].CC(C)=O>[CH2:14]([O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:7]=1[O:8][CH3:9])[CH:2]=[O:1])[CH:13]=[CH2:12]

Participants

5

Reactant 2

HCID 7841Allyl bromideHCID 12127Isovanillin

Product 1

HCID 5341483-Allyloxy-4-methoxybenzaldehydeYield 88.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 11430Potassium CarbonateSolvent

Procedure

Isovanillin (76 g) was dissolved in a stirred mixture of potassium carbonate (104 g) and acetone (450 mls) followed by the dropwise addition of allyl bromide (67 g) over ca. 20 mins. The mixture was refluxed for 5 hours, cooled and filtered. The solvent was removed from the filtrate under reduced pressure and the residue was distilled under vacuum to yield 3-allyloxy-4-methoxybenzaldehyde (85 g), b.p. 1.37-150° C. at 1.5 mbar.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe solvent was removed from the filtrate under reduced pressure
  5. distillationthe residue was distilled under vacuum

Sources & evidence

ORD record
ord-09ab3df37bca49d3a840f99ab293d716
Source dataset
uspto-grants-1991_06
Patent number
US05021512

Reaction notes

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