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Functional polymers. XVI. Synthesis and polymerization of 2(2-hydroxy-5-isopropenylphenyl)-2H-benzotriazole and a new synthesis of 2(2-hydroxy-5-vinylphenyl)2H-benzotriazole

✍ Scribed by Nir, Zohar ;Vogl, Otto ;Gupta, Amitava

Publisher
John Wiley and Sons
Year
1982
Weight
973 KB
Volume
20
Category
Article
ISSN
0360-6376

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✦ Synopsis

Abstract

2(2‐Hydroxy‐5‐isopropenylphenyl)2H‐benzotriazole was synthesized in 40% overall yield starting from o‐nitroaniline. Diazotization in aqueous hydrochloric acid gave o‐nitrophenyl diazonium chloride which was condensed with p‐hydroxyacetophenone; the azo compound was reduced to 2(2‐hydroxy‐5‐acetylphenyl) 2H‐benzotriazole with zinc powder in sodium hydroxide solution and the 2‐hydroxy group of the compound was acetylated. Treatment of the acetyl compound with methyl Grignard reagent resulted in the methylation of the 5‐acetyl group to 2[2‐acetoxy‐5(2‐hydroxy‐2‐propyl)phenyl]2H‐benzotriazole which was then dehydrated with potassium hydrogen sulfate to the desired 2(2‐hydroxy‐5‐isopropenylphenyl)2H‐benzotriazole. This monomer did not homopolymerize, but was copolymerized readily with styrene, methyl methacrylate, and n‐butyl acrylate with azobisisobutyronitrile as the initiator. 2(2‐Acetoxy‐5‐acetylphenyl)2H‐benzotriazole was also reduced with sodium borohydride to form 2[2‐acetoxy‐5‐(1‐hydroxyethyl)phenyl]2H‐benzotriazole which was dehydrated and hydrolyzed to the known 2(2‐hydroxy‐5‐vinylphenyl)‐2H‐benzotriazole. This route provides a novel and simpler synthesis of 2(2‐hydroxy‐5‐vinylphenyl)2H‐benzotriazole.

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