3 - Nitro - 4 - Chloro-amyl Benzene Synthesis And Process Research

3-Nitro-4-chloropentylbenzene is a kind of important organic chemical intermediate and material, which can be used widely in the field of medicine, pesticide, veterinary pharmaceutical and other fine chemicals industry.The object product was synthesized by Friedel-Crafts acylation, Wolff-kishner-Huang reduction and nitration using chlorobenzene as starting material. The synthetic effects on the reaction were investigated such as amount of catalyst, reaction temperature and reaction time in the acylation process; reaction temperature, reaction time, amount of catalyst and ratio of materials in reduction process; reaction temperature, base acid, composition of mix acid (HNO₃/H₂SO₄), reaction time and ratio of materials. The optimal synthetic technology was as follows: acylation at 100℃for 1h with the mole ratio of catalyst AlCl₃ to n-pentanoyl chloride being 1:4; reduction using 3 equiv. of NH₂NH₂ and 0.5 equiv. of KOH with the decomposition of hydrazone at 180℃for 4h; nitration at 70℃for 5h using HNO₃: H₂SO₄: H₂O = 68: 28: 4 (mass ratio) as nitrating agent in the absence of base acid H₂SO₄ with the mole ratio of HNO₃ to p-chloropentylbenzene being 2:1. The total yield of object product was 31.8% based on the chlorobenzene.