2,4-Dihydroxybenzaldehyde → 2,4-Bis(benzyloxy)benzaldehyde

HRID 728068Notes

Reaction equation

HRID 728068 reaction equation
[OH:1][C:2]1[CH:9]=[C:8](O)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:19](=[O:22])([O-])[O-].[Na+].[Na+]>C(O)C>[CH2:11]([O:1][C:2]1[CH:9]=[C:8]([O:22][CH2:19][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:3]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 72132,4-DihydroxybenzaldehydeHCID 7503Benzyl ChlorideHCID 10340Sodium Carbonate

Product 1

HCID 18090802,4-Bis(benzyloxy)benzaldehydeYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,4-Dihydroxybenzaldehyde (14.5 g) was dissolved in ethanol (60 ml) and then thereto were added benzyl chloride (30 ml) and sodium carbonate (1.7 g), followed by reflux under heating for 5 hours. Insoluble matters were removed by filtration. The filtrate was allowed to stand for cooling and then the produced solid was collected by filtration and recrystallized from ethanol to obtain 2,4-dibenzyloxybenzaldehyde (20 g, yield 60%). Melting point: 89°-90° C.

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 5 hours
  3. customInsoluble matters were removed by filtration
  4. temperaturefor cooling
  5. filtrationthe produced solid was collected by filtration
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-930c6bfd53094ce29ddaf9a8604e665d
Source dataset
uspto-grants-1991_09
Patent number
US05047430

Reaction notes

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