Benzyl Bromide → 2-benzyloxy-3-methylbenzaldehyde

HRID 1422316Notes

Reaction equation

HRID 1422316 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[CH2:17]([O:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5227773-Methylsalicylaldehyde

Product 1

HCID 110641372-benzyloxy-3-methylbenzaldehydeYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

2-Hydroxy-3-methylbenzaldehyde 20.0 g (147 mmol) prepared by the above 1-(1) was dissolved in dimethylformamide (DMF) (100 ml) and to the solution was added potassium carbonate 31.0 g (221 mmol) and thereto was dropped benzyl bromide 25.0 g (147 mmol). The reaction mixture was stirred for 2 hours at 20° C. After disappearance of the raw material, the reaction mixture was filtrated and the solvent was removed in vacuo and the residue was purified in the same manner as in the above 2-(1) to give 2-benzyloxy-3-methylbenzaldehyde 24.2 g (yield: 73%).

Workup

  1. filtrationAfter disappearance of the raw material, the reaction mixture was filtrated
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified in the same manner as in the above 2-(1)

Sources & evidence

ORD record
ord-5bc23b1c2d6242a7a2a6366d3082fcc1
Source dataset
uspto-grants-2000_06
Patent number
US06080895

Reaction notes

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