Ethanol → 3-Benzyloxybenzaldehyde

HRID 2254420Notes

Reaction equation

HRID 2254420 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:15]([OH:17])[CH3:16]>>[CH2:7]([O:17][C:15]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:16]=1)[CH:1]=[O:4])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 743423-BenzyloxybenzaldehydeYield 81.1%

Procedure

15.0 g of m-hydroxybenzaldehyde was dissolved in 200 ml of ethanol, and 25.0 g of potassium carbonate and 32 g of benzyl bromide were added. With stirring, the mixture was heated under reflux for 6 hours. After the reaction, the insoluble inorganic salts were removed by filtration. The filtrate was evaporated under reduced pressure, and purified by silica gel column chromatography [Wakogel C-200, 150 g; hexane/chloroform=1/1] and then recrystallized from hexane to give 21.1 g (yield 81.1%) of 3-benzyloxybenzaldehyde having a melting point of 56° to 57° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. customAfter the reaction
  4. customthe insoluble inorganic salts were removed by filtration
  5. customThe filtrate was evaporated under reduced pressure
  6. custompurified by silica gel column chromatography [Wakogel C-200, 150 g; hexane/chloroform=1/1]
  7. customrecrystallized from hexane

Sources & evidence

ORD record
ord-727aa2523dd74f9ca0ca969b07cb1fe7
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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