Benzyl Bromide → 3,4-Bis(benzyloxy)benzaldehyde

HRID 1654937Notes

Reaction equation

HRID 1654937 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1O)[CH:5]=[O:6].[C:11](=[O:14])([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH2:17]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:14][CH2:11][C:2]1[CH:3]=[CH:4][CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 795263,4-Bis(benzyloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3,4-dihydroxy-benzaldehyde (2.76 g, 20 mmol) in dry acetone (50 ml), potassium carbonate (5.52 g, 40 mmol) and benzylbromide (5 ml, 42 mmol) was heated at reflux for 12 hours. The mixture was cooled to room temperature, potassium carbonate was removed by filtering the solution and the filtrate was concentrated to a powder which was recrystallized from acetone to yield (5.4 g, 81%) ether as prisms, mp 89°-90° (lit. mp 90°) IR υmax 1685, 1595, 1483, 1508, 1454, 1434, 1269, 1132, 695, 650 cm-1 ; and 1H-NMR (90 MHz), 5.21 (2H, s, ArCH2O), 5.26 (2H, s, ArCH20), 7.02 (1H, d, J=7.9 Hz), 7.30-7.50 (12H, ArH), 9.81 (1H, s, CHO). Anal. calcd for C21H18O3 : C, 79.23; H, 5.70. Found: C, 79.26;H, 5.68.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hours
  3. custompotassium carbonate was removed
  4. filtrationby filtering the solution
  5. concentrationthe filtrate was concentrated to a powder which
  6. customwas recrystallized from acetone
  7. customto yield (5.4 g, 81%) ether as prisms, mp 89°-90° (lit. mp 90°) IR υmax 1685, 1595, 1483, 1508, 1454, 1434, 1269, 1132, 695, 650 cm-1

Sources & evidence

ORD record
ord-6716c695fc5a4b93b27f0a7f011c5552
Source dataset
uspto-grants-1995_04
Patent number
US05409953

Reaction notes

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