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

HRID 322859

Reaction equation

HRID 322859 reaction equation
[OH:1][C:2]1[CH:9]=[C:8](O)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[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>CN(C)C=O>[CH2:17]([O:1][C:2]1[CH:9]=[C:8]([O:14][CH2:11][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:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 72132,4-DihydroxybenzaldehydeHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 18090802,4-Bis(benzyloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,4-dihydroxybenzaldehyde (17.5 g), potassium carbonate (42 g) and benzyl bromide (35 mL) in dimethyl formamide (100 mL) is stirred at room temperature for 18 hours. The reaction mixture is poured into vigorously stirred ice-water (300 mL) and stirring is continued for 30 minutes. The resulting brown solid is filtered and dried to give 2,4-dibenzyloxybenzaldehyde (28.5 g), m.p. 80-81° C. [Elemental analysis:- C,79.5; H,6.10%. Calculated:- C,79.2; H,5.70%].

Workup

  1. stirringstirring
  2. waitis continued for 30 minutes
  3. filtrationThe resulting brown solid is filtered
  4. customdried

Sources & evidence

ORD record
ord-e50d84db859746ba8e85e32b274244f3
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Linked notes

Loading…