Benzyl Bromide → 2-benzyloxy-3-methylbenzaldehyde

HRID 1422315Notes

Reaction equation

HRID 1422315 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].[H][H].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O.O>[CH2:15]([O:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5227773-MethylsalicylaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 110641372-benzyloxy-3-methylbenzaldehydeYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 2-hydroxy-3-methylbenzaldehyde 20.0 g (147 mmol) prepared by the above 1-(1) in dimethylformamide (DMF) (100 ml) was added to the suspension of sodium hydride 6.5 g (163 mmol) with purity 60% and DMF (40 ml) under ice-cooling. After completion of emission of hydrogen gas, benzyl bromide 25.0 g (147 mmol) was dropped to it in a ice bath. The reaction mixture was stirred for 4 hours at 20° C. After the disappearance of the raw material, water was added to the reaction mixture and it was extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed in vacuo and the residue was purified by silica gel chromatography (n-hexane-ethyl acetate) to give 2-benzyloxy-3-methylbenzaldehyde 29.9 g (yield: 91%).

Workup

  1. temperaturecooling
  2. extractionwas extracted with methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customthe residue was purified by silica gel chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2746587cf32144be97be7a78c86bf818
Source dataset
uspto-grants-2000_06
Patent number
US06080895

Reaction notes

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