Benzyl Bromide → 2-(Benzyloxy)-3,4-dimethoxybenzaldehyde

HRID 2228505Notes

Reaction equation

HRID 2228505 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[C:17]([O:18][CH3:19])=[C:16]([O:20][CH3:21])[CH:15]=[CH:14][C:11]=1[CH:12]=[O:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:9][C:10]1[C:17]([O:18][CH3:19])=[C:16]([O:20][CH3:21])[CH:15]=[CH:14][C:11]=1[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 879993,4-Dimethoxysalicylaldehyde

Product 1

HCID 8195792-(Benzyloxy)-3,4-dimethoxybenzaldehydeYield 91.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyl bromide (12.9 ml, 0.108 mol) was added to a suspension of 2-hydroxy-3,4-dimethoxybenzaldehyde (19 g, 0.104 mol) and potassium carbonate (14.41 g, 0.104 mol) in acetone (200 ml) and the reaction stirred at reflux for 3 hours. On cooling, the mixture was concentrated under reduced pressure and the residue partitioned between water (150 ml) and dichloromethane (150 ml). The organic layer was filtered through silica, washing through with hexane and then ethyl acetate. Evaporation of the filtrate under reduced pressure gave a yellow gum. The crude product was purified on silica gel eluting with ethyl acetate:hexane (30:70 v/v) to give the subtitle compound (25.9 g, 88%). Rf 0.82 (ethyl acetate:hexane 1:1, v/v). MS m/z 273 (MH)+.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureOn cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customthe residue partitioned between water (150 ml) and dichloromethane (150 ml)
  5. filtrationThe organic layer was filtered through silica
  6. washwashing through with hexane
  7. customEvaporation of the filtrate under reduced pressure
  8. customgave a yellow gum
  9. customThe crude product was purified on silica gel eluting with ethyl acetate:hexane (30:70 v/v)

Sources & evidence

ORD record
ord-ef0a4f31d96848de8a25d57846d29880
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

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