Water → 2,4-Bis(benzyloxy)benzaldehyde

HRID 1442526Notes

Reaction equation

HRID 1442526 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.O>CN(C)C=O.CCCCCC>[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

7

Reactant 4

HCID 962WaterHCID 72132,4-DihydroxybenzaldehydeHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 18090802,4-Bis(benzyloxy)benzaldehydeYield 167.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a solution of 2,4-dihydroxybenzaldehyde (5.00 g, 36.2 mmol) in N,N-dimethylformamide (30 ml) were added potassium carbonate (12.0 g, 86.9 mmol) and benzyl bromide (9.48 ml, 79.6 mmol). After stirring at room temperature for 3 hr 30 min, water (100 ml) and hexane (50 ml) were added, and the precipitated solid was collected by filtration. The solid was washed with water (3 ml×3) and hexane (5 ml) and dried under reduced pressure to give 2,4-bisbenzyloxybenzaldehyde (9.67 g, yield 84%).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washThe solid was washed with water (3 ml×3) and hexane (5 ml)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-3e64691058194355878add906c5d7467
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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