Wang Jia-an
2012
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Journal
Modern Chemical Industry
Abstract
E-2,5-diacetamido-2′4′-dimethoxy-4-nitrostilbene(DADMNS) is synthesised in this study,which is an important intermediate of second order nonlinear optical materials.2,5-Diacetamido-4-nitrotoluene(DANT) is prepared from 2,5-diaminotoluene via acetylation and nitration.2,4-Dimethoxybenzaldehyde(DMBA) is obtained from 1,3-dimethoxybenzene by Vilsmeier-Haack reaction in the presence of DMF and POCl3.With piperdine as catalyst and molecular sieve as dehydrating agent,DANT undergoes a condensation with DMBA in DMF to give the target product DADMNS.The yield and the purity are 73.20% and 98.89%,respectively.The chemical structure of the target product is confirmed by IR,1H-NMR,and 13C-NMR.The optimal reaction parameters are shown as follows:1∶2 of the ratio of DANT to DMBA,0.01 mol of DANT,2.5 mL of piperidine,25 mL of DMSO,3.0 g of molecular sieve,130℃ of reaction temperature and 1 hour of reaction time.