1,2-Dimethylpyridinium iodide → 1-Methyl-2-[o-(2,2-dimethoxyethoxy)-styryl]pyridinium iodide

HRID 1577286

Reaction equation

HRID 1577286 reaction equation
[I-:1].[CH3:2][N+:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9].[CH3:10][O:11][CH:12]([O:23][CH3:24])[CH2:13][O:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=O>CO.N1CCCCC1>[I-:1].[CH3:2][N+:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[CH:17][C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=1[O:14][CH2:13][CH:12]([O:23][CH3:24])[O:11][CH3:10]

Participants

5

Reactant 2

HCID 701071,2-Dimethylpyridinium iodideHCID 205720342-(2,2-Dimethoxyethoxy)benzaldehyde

Product 1

HCID 705758631-Methyl-2-[o-(2,2-dimethoxyethoxy)-styryl]pyridinium iodideYield 87%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 887MethanolSolvent

Procedure

In 6 ml of methanol, 1.50 g of 1,2-dimethylpyridinium iodide and 1.50 g of o-(2,2-dimethoxyethoxy)benzaldehyde. The resultant solution, with two drops of piperidine added thereto, was refluxed for five hours and then left to stand and cool off. The crystals which deposited consequently were collected and thoroughly washed with acetone. Consequently, there was obtained 2.36 g of 1-methyl-2-[o-(2,2-dimethoxyethoxy)-styryl]pyridinium iodide which melted at 169°~173° C. This product showed the highest absorption at 353 nm (ε=1.78×104). The infrared absorption spectrum (KBr) showed peaks at 1630, 1610, 1595, 1567, 1515, 1500, 1450, 1280, 1248, 1130, 1065, 971, 780, 760 and 750 cm-1. The yield was 87%.

Workup

  1. temperaturewas refluxed for five hours
  2. waitleft
  3. temperaturecool off
  4. customThe crystals which deposited consequently were collected
  5. washthoroughly washed with acetone

Sources & evidence

ORD record
ord-ec75d7a706e44f4081940988e2de3279
Source dataset
uspto-grants-1981_09
Patent number
US04287335

Linked notes

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