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Citation: ZHANG Jian-Ting, MAO Lian-Cheng, WANG Jia-An, HU Jian-Min, JIN Ning-Ren. Synthesis of Methyl 4-(5-Nitro-6-hydroxybenzoxazol-2-yl) benzoate[J]. Chinese Journal of Applied Chemistry, ;2009, 26(9): 1040-1044. shu

Synthesis of Methyl 4-(5-Nitro-6-hydroxybenzoxazol-2-yl) benzoate

1.
a College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014;
2.
b Hangzhou Dragon Chemical Co.Ltd, Hangzhou

Corresponding author: JIN Ning-Ren,
Received Date: 19 August 2008
Available Online: 29 December 2008
Fund Project: 江苏省科技攻关重大项目(BE2006077) (BE2006077)

The synthesis of methyl 4-(5-nitro-6-hydroxybenzoxazol-2-yl) benzoate(MNB),an AB-type monomer precursor for a new AB-type poly(p-phenylene benzobizoxazole) (PBO) was studied,and the synthesis of MNB from 4-amino-6-nitroresorcinol hydrochloride(ANR·HCl) and mono-methyl terephthalate(MTA) was developed by means of acyl chlorination,condensation and cyclization separately or in situ synthesis.The optimum conditions were methyl isobutyl ketone as solvent,feed ratio(mol ratio) of ANR·HCl/MTA of 1.00:1.03,and condensation reaction at 115 ℃ for 2.5 h.Cyclization reaction at 120 ℃ for 8.5 h after adding PPA as dehydrating agent at a feed ratio(mass ratio) of ANR·HCl/PPA of 1.00:3.25,the product was obtained with a yield of 75.68% and the purity of MNB without further purification was 96.32% by HPLC method.Structures of the products were characterized by ¹H NMR and IR.
- methyl(nitrohydroxybenzoxazolyl) benzoate,
- monomer precursor,
- aminonitroresorcinol hydrochloride,
- condensation-cyclization reaction,
- in situ synthesis
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