Benzyl Bromide → 2-(Benzyloxy)-3-methoxybenzaldehyde

HRID 1982178Notes

Reaction equation

HRID 1982178 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:5]([CH:6]=[O:7])[C:4]=1[OH:11].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:12]([O:11][C:4]1[C:3]([O:2][CH3:1])=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8991o-VanillinHCID 11430Potassium Carbonate

Product 1

HCID 12680872-(Benzyloxy)-3-methoxybenzaldehydeYield 98.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

50 g (0.3 mole) of 3-methoxysalicylaldehyde are heated to reflux for 3 hours with 51.3 g (0.3 mole) of benzyl bromide and 48.4 g of potassium carbonate in 300 ml of acetone. After filtration, the filtrate is concentrated. 71.8 g of the title compound are obtained as a yellow oil.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-dfe8a0ba1a0f4aa6a4347c8db1a1b032
Source dataset
uspto-grants-1986_06
Patent number
US04595685

Reaction notes

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