Synthesis of (S)-5-Chloro-2-hydroxy-2-methoxycarbonyl-1-indanone

(S)-5-Chloro-2-hydroxy-2-methoxycarbonyl-1-indanone is an important intermediate for the synthesis of chiral insecticide,indoxacarb.It was prepared from 5-chloro-2-methoxycarbonyl-1-indanone through asymmetric hydroxylation.The effects of solvent,oxidant and catalyst,etc.on the yield and the ee value of the product were investigated in detail.The preferential synthesis condition was as follows:n(5-chloro-2-methoxycarbonyl-1-indanone)∶n(cinchonine)∶n(cumyl hydroperoxide)=1∶0.2∶1.2,in CH2Cl2 solvent,at room temperature,for 5 h reaction time.The post treatment method of the product was improved by recrystallizing from ethyl acetate instead of the column separation.The yield of the reaction was above 82% and the ee value of the targeted product was increased up to 92%,with [α]20D=+108.8°(10 g/L,CHCl3),m.p.160.1～162.3 ℃.The product was characterized by FTIR、1HNMR、13CNMR and MS.The experimental results provide with the important basic data for the industrial development of the product in the cooperation company.