3-Hydroxybenzaldehyde → 3-[(2,6-Dichlorobenzyl)oxy]benzaldehyde

HRID 2300585Notes

Reaction equation

HRID 2300585 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:12]=1[CH2:13]Br.[H-].[Na+]>CN(C)C=O>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:12]=1[CH2:13][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 24758Sodium hydrideHCID 301591-Bromomethyl-2,6-dichlorobenzene

Product 1

HCID 7354843-[(2,6-Dichlorobenzyl)oxy]benzaldehydeYield 107.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxybenzaldehyde (3.59 g, 24.39 mmol) and 2,6-dichlorobenzyl bromide (7.05 g, 29.39 mmol) in dimethylformamide (20 mL) at 0° C. was added 60% sodium hydride (1.176 g, 29.39 mmol). After stirring at ambient temperature for 16 h, the reaction was partitioned between ethyl acetate and water. The organic layer was washed with aqueous sodium chloride and dried (MgSO4). Purification by flash column chromatography (silica gel, hexane/ethyl acetate) yielded the title compound as an off-white solid (7.38 g, 89%).

Workup

  1. customthe reaction was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with aqueous sodium chloride
  3. dry with materialdried (MgSO4)
  4. customPurification by flash column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dcdecd14a1f84e189688701b493a669d
Source dataset
uspto-grants-2002_12
Patent number
US06498187B1

Reaction notes

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