4-Hydroxybenzaldehyde → 4-[(1-Trityl-4-imidazolyl)methoxy]benzaldehyde

HRID 361929

Reaction equation

HRID 361929 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl[CH2:11][C:12]1[N:13]=[CH:14][N:15]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:17]([N:15]1[CH:16]=[C:12]([CH2:11][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[N:13]=[CH:14]1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 27631764-(Chloromethyl)-1-trityl-1H-imidazole

Product 1

HCID 154290374-[(1-Trityl-4-imidazolyl)methoxy]benzaldehydeYield 51.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.22 g of p-hydroxybenzaldehyde and 4.08 g of 4-chloromethyl-1-tritylimidazole were dissolved in 40 ml of N,N-dimethylformamide, followed by adding 1.66 g of anhydrous potassium carbonate and subsequently stirring at room temperature for 40 hours. The thus prepared reaction solution were partitioned between water and benzene, and the resulting organic layer was concentrated to dryness. The resulting residue was purified by subjecting it to silica gel column chromatography using chloroform as an elution solvent, and the thus purified product was crystallized from a n-hexane/benzene solvent system. In this way, 2.3 g of the title compound was obtained.

Workup

  1. customThe thus prepared reaction solution
  2. customwere partitioned between water and benzene
  3. concentrationthe resulting organic layer was concentrated to dryness
  4. customThe resulting residue was purified
  5. customthe thus purified product was crystallized from a n-hexane/benzene solvent system

Sources & evidence

ORD record
ord-fcc0d6724e844e9e9a7ffaa28afc14fa
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Linked notes

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