3-Chlorophenol → 4-(3-Chlorophenoxy)benzaldehyde

HRID 440576Notes

Reaction equation

HRID 440576 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.F[C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1.[H-].[Na+]>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 79333-ChlorophenolHCID 24758Sodium hydrideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 108472144-(3-Chlorophenoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Chlorophenol (1.9 g) was stirred with 4-fluoro-benzaldehyde (1.8 g) and sodium hydride (0.46 g of an 80% suspension in oil) in dimethylformamide (50 ml) at 110° C. under an atmosphere of nitrogen for 16 hours. The solution was diluted with water and extracted with diethyl ether. The ethereal extract was dried (Na2SO4), concentrated and purified by chromatography on silica gel eluting with ethyl acetate-petroleum ether (1:9) to give the title compound as a colourless oil.

Workup

  1. extractionextracted with diethyl ether
  2. extractionThe ethereal extract
  3. dry with materialwas dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by chromatography on silica gel eluting with ethyl acetate-petroleum ether (1:9)

Sources & evidence

ORD record
ord-adf6b17e5a4a457bb97a4f58c785175d
Source dataset
uspto-grants-1996_05
Patent number
US05519163

Reaction notes

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