The Reaction of Dihalotetramethylbenzenes with Fuming Nitric Acid as a New Convenient Route to Some Dihalotrimethylbenzylic Compounds

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概要

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• Products obtained by the nitration of three isomeric dichloro and dibromotetramethylbenzenes with fuming nitric acid have been investigated. 3,6-Dihalo-1,2,4,5-tetramethylbenzene (dihalodurene) gave mainly 3,6-dihalo-2,4,5-trimethylbenzyl nitrate or 1,2-bis(nitrooxymethyl)-3,6-dihalo-4,5-dimethylbenzene, depending on the reaction temperature and the amount of nitrating agent. 4,6-Dihalo-1,2,3,5-tetramethylbenzene (dihaloisodurene) yielded a mixture of 3,5-dihalo-2,4,6-trimethylbenzyl nitrate and 2,6-dihalo-3,4,5-trimethylbenzyl nitrate, the latter in somewhat greater amount. 5,6-Dihalo-1,2,3,4-tetramethylbenzene (dihaloprehnitene) gave 5,6-dihalo-2,3,4-trimethylbenzyl nitrate as the sole nitrooxylation product. The reaction affords a new convenient route to precursors of various polysubstituted benzylic compounds hitherto not easily obtained by ordinary methods. Physical properties of some dihalotrimethylbenzylic compounds (chloride, nitrate, acetate, alcohol, and bisbenzyl ether) have been recorded.

• 公益社団法人 日本化学会の論文

著者

• Suzuki Hitomi

  Deparment Of Chemistry School Of Science Kwansei Gakuin University

• Nakamura Kiyomi

  Department of Chemistry, Faculty of Science, Kyoto University

• Takeshima Michiko

  Department of Chemistry, Faculty of Science, Kyoto University

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