Pyridine → HCID 18433807, compound

HRID 849366Notes

Reaction equation

HRID 849366 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].N1C=CC=CC=1.I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH3:11][O:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[O:1][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:6]=[O:7]

Participants

6

Reactant 4

HCID 1049PyridineHCID 1183VanillinHCID 11430Potassium CarbonateHCID 11575Iodobenzene

Product 1

HCID 18433807HCID 18433807, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
145 °C

Procedure

6.0 g of 4-hydroxy-3-methoxybenzaldehyde, 75 ml of pyridine, 12.0 g of iodobenzene, 10.9 g of potassium carbonate and 6.24 g of cupric oxide were mixed and heated at 145° C. for 18 hours in a sealed tube. The reaction solution was left to cool to room temperature and then diluted with ethyl acetate and subjected to celite filtration. The filtrate was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to obtain 1.11 g (yield: 12%) of the above identified compound as a colorless oily substance.

Workup

  1. waitThe reaction solution was left
  2. temperatureto cool to room temperature
  3. filtrationsubjected to celite filtration
  4. distillationThe filtrate was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)
  6. customto obtain 1.11 g (yield: 12%) of the

Sources & evidence

ORD record
ord-29cb93029f7d4e7d8965552475a5e3f7
Source dataset
uspto-grants-2000_01
Patent number
US06011174

Reaction notes

Loading…