三氟甲烷磺酸催化1-茚酮氧化反应的研究

Studies on the oxidation of 1-indanone catalyzed by trifluoromethanesulfonic acid

研究了三氟甲烷磺酸(HOTf)催化氧化1-茚酮的性能,考察了HOTf、H2O2的用量、反应时间、反应温度和溶剂等几个因素对反应的影响,并与用其它几种质子酸的反应结果进行了比较.研究结果表明,以HOTf为催化剂时反应效果最好,0.1 g 1-茚酮在0.5 mL HOTf、0.32 mL 30%H2O2和2 mL 2,2,3,3-四氟-1-丙醇(TFP)体系中,恒温60℃反应4 h,转化率可以达到86%,产物邻羟基苯丙酸的选择性达98%.可能的反应机理是:1-茚酮先经过Baeyer-Villiger反应生成二氢香豆素,后者进一步水解得到邻羟基苯丙酸.

The oxidation of 1-indanone was studied, in which trifluoromethanesulfonic acid （HOTf） was used as cat- alyst and 30MH202 as the oxidant. The effects of the dosage of HOTf, addition amount of H202, reaction time, reaction temperature and solvents were investigated. Other proton acid catalysts were also tested to compare with HOTf. The results indicated that the optimal catalyst is HOTf. Under the reaction conditions of 0.1 g 1-indanone, 0.5 mL HOTf, 0.32 mL 30%H202 and 2 mL 2,2,3,3-tetrafluoro-propanol （TFP） at 60 ℃ for 4 h, the conversion of 1-indanone was 86%, while the selectivity of o-hydroxyl-phenylpropyl acid reached 98%. The possible mecha- nism is that dihydroeoumarin is formed firstly by Baeyer-Villiger rearrangement, then it is hydrolyzed into o-hydrox- yl-phenylpropionic acid under aqueous acid condition.