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

HRID 1738708Notes

Reaction equation

HRID 1738708 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-4ab3b6ab2e144e868577125647162fe5
Source dataset
uspto-grants-1999_10
Patent number
US05962695

Reaction notes

Loading…