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

HRID 1577287Notes

Reaction equation

HRID 1577287 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:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O>CO.N1CCCCC1>[I-:1].[CH3:2][N+:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[CH:18][C:17]1[CH:20]=[CH:21][CH:22]=[C:15]([O:14][CH2:13][CH:12]([O:23][CH3:24])[O:11][CH3:10])[CH:16]=1

Participants

5

Reactant 2

HCID 701071,2-Dimethylpyridinium iodideHCID 20572041m-(2,2-Dimethoxyethoxy)benzaldehyde

Product 1

HCID 705758711-Methyl-2-[m-(2,2-dimethoxyethoxy)-styryl]pyridinium iodideYield 86%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 887MethanolSolvent

Procedure

In 6 ml of methanol, 1.50 g of 1,2-dimethyl pyridinium iodide and 1.50 g of m-(2,2-dimethoxyethoxy)-benzaldehyde were dissolved. The resultant solution, with two drops of piperidine added thereto, was refluxed for five hours and thereafter cooled off. Consequently, crystals were deposited. When the crystals were collected and washed thoroughly with acetone, there was obtained 2.34 g of 1-methyl-2-[m-(2,2-dimethoxyethoxy)-styryl]pyridinium iodide. In water, this product showed the highest absorption at 336 nm (ε=2.13×104). The infrared absorption spectrum (KBr) showed peaks at 1620, 1600, 1580, 1268, 1137, 1068, 965, 840, 772 and 680 cm-1. The yield was 86%.

Workup

  1. temperaturewas refluxed for five hours
  2. temperaturecooled off
  3. customWhen the crystals were collected
  4. washwashed thoroughly with acetone

Sources & evidence

ORD record
ord-37d5fd755cec42079094b51892d6723f
Source dataset
uspto-grants-1981_09
Patent number
US04287335

Reaction notes

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