4-Hydroxybenzaldehyde → 4-[(2,6-dichlorobenzyl)oxy]benzaldehyde

HRID 411737Notes

Reaction equation

HRID 411737 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[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:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 24758Sodium hydrideHCID 301591-Bromomethyl-2,6-dichlorobenzene

Product 1

HCID 7354664-[(2,6-dichlorobenzyl)oxy]benzaldehydeYield 107.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-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-5d7a1c1838f54022afafa11675904a05
Source dataset
uspto-grants-2003_05
Patent number
US06559179B1

Reaction notes

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