Dimethylformamide → Terephthalaldehyde

HRID 1068252Notes

Reaction equation

HRID 1068252 reaction equation
C1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:27]C1C=C(CBr)C(OCCCCCCC)=CC=1CBr)CCCCCC.CN(C)[CH:48]=[O:49]>>[PH4+:7].[CH:48](=[O:49])[C:14]1[CH:15]=[CH:16][C:17]([CH:20]=[O:27])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 11776Triphenylphosphine2×HCID 184319151,4-Bis(bromomethyl)-2,5-bis(heptyloxy)benzene

Product 2

HCID 12173TerephthalaldehydeHCID 5460504Phosphonium

Procedure

A phosphonium salt (A) was synthesized by the reaction of 2,5-diethyl-P-xylylene dibromide with triphenylphosphine in an N,N-dimethylformamide solvent, and a phosphonium salt (B) was synthesized by the reaction of 2,5-diheptyloxy-p-xylylene dibromide with triphenylphosphine in an N,N-dimethylformamide solvent. The obtained two phosphonium salts (A) (4.1 parts by weight) and (B) (1.0 part by weight) and terephthalaldehyde (0.8 parts by weight) were dissolved in ethyl alcohol. For a 3-hour polymerization, an ethyl alcohol solution containing 0.8 parts by weight of lithium ethoxide was added dropwise to an ethyl alcohol solution of the phosphonium salts and dialdehyde at room temperature. After allowed to stand alone at room temperature overnight, the reaction solution was subjected to fractionation by precipitation. The precipitate was then filtered out, washed with ethyl alcohol, and dissolved in chloroform, to which ethanol was added for re-precipitation. The obtained product was dried under reduced pressure to obtain 0.35 parts by weight of the end polymer. This is called a polymeric fluorescent substance 1. Set out below are the repeating unit in polymeric fluorescent substance 1 and its molar ratio calculated from the charge ratio of monomers.

Sources & evidence

ORD record
ord-c102be5497eb4b788b2a1a089d5ef89f
Source dataset
uspto-grants-2001_06
Patent number
US06249085B1

Reaction notes

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