Synthesis Of 1-Chloro-4-propoxythioxanthone And Investigation Of Diphenylammonium Triflate Catalyzed Reactions

In this dissertation, We disclosed our research results on the synthesis of 1-chloro-4-propoxythioxanthone(CPTX) and catalytic properties of organic catalyst, 4-(nitro)-diphenylammonium triflate(NDPAT) in esterifications and Friedel-Crafts reactions.(l)We first introduced 2-mercapto benzoic acid replacing 2,2-dithiobisbenzoic acid as a raw material in preparation of l-chloro-4-propoxythioxanthone(CPTX). The title compound was synthesized in a excellent yield. The total yield reached 84.9%. That is about 30% more than in literature. In our research, we found that the quantity of sulphuric acid and temperature were main factors in reactions. The reaction conditions were optimized. (2)A novel organic catalyst, 4-(nitro)-diphenylammonium triflate(NDPAT) was prepared from 4-nitrochlorobenzene with aniline through a Goldberg synthesis and acidification. It was found that NDPAT efficiently catalyzed esterification between equimolar amounts of carboxylic acids and alcohols in good yields under mild reaction conditions. The efficacy of various catalysts such as DPAT, NDPAT, PADPAT, triflic acid, sulphuric acid and TsOH were studied in esterifications. Triflic acid was found to be the most effective catalyst. Moreover a little water could speed the reaction catalyzed byNDPAT.(3) We explored the reactivity of NDPAT in Friedel-Crafts reactions. It was found that NDPAT could effectively catalyze the benzylation of aromatic compounds with benzyl alcohol. But for cyciohexanol and chloride benzyl, NDPAT lost the activity.