3-Hydroxybenzaldehyde → 3-[(4-chlorobenzyl)oxy]benzaldehyde

HRID 1079102Notes

Reaction equation

HRID 1079102 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][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.O>CN(C)C=O>[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 22728543Water ethylacetate

Product 1

HCID 6933013-[(4-chlorobenzyl)oxy]benzaldehydeYield 78.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1.2 g of 3-hydroxybenzaldehyde in 50 ml of N,N-dimethylformamide were added 2.4 g of 4-chlorobenzyl chloride and 2.1 g of potassium carbonate. The mixture was stirred at 60° C. for 3 hours. After cooling, the reaction mixture was treated with ethyl acetate-water. The resulting ethyl acetate layer was separated, washed with water, dried with anhydrous magnesium sulfate, and subjected to vacuum distillation to remove the solvent. The resulting residue was purified by silica gel column chromatography (eluant: n-hexane/ethyl acetate=102) to obtain 1.9 g of 3-(4-chlorobenzyloxy)benzaldehyde.

Workup

  1. temperatureAfter cooling
  2. customThe resulting ethyl acetate layer was separated
  3. washwashed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationsubjected to vacuum distillation
  6. customto remove the solvent
  7. customThe resulting residue was purified by silica gel column chromatography (eluant: n-hexane/ethyl acetate=102)

Sources & evidence

ORD record
ord-0edd15d40248420f9ffe5a052e7a73c1
Source dataset
uspto-grants-1996_08
Patent number
US05550292

Reaction notes

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