Study On Synthesis And Application Of Chrial 2,2’-dimethoxy-1,1’-binaphthyl

The thesis involves four parts. In the first part, FeCl3·6H2O was used to catalyze the oxidative coupling reaction of 2-naphthol. Then alkaline and acid solution was used to purify BINOL respectively. The purity and the yield of BINOL was about 99.73%,91.2%. The method is simple and economic.In the second part, first of all, chloride N-benzyl-cinchoninium is synthesized in 90% yield. [a]26=+165°(c=0.003, H2O)。Then neutralization of the combined HCl extracts with sodium bicarbonate led to white precipitates in 90% recovery which could be further used for resolution without any decrese in efficiency.In the third part, it’s about optical resolution of BINOL(1) resolution of BINOL using N-benzyl-cinchoniniumThe R-BINOL was gained in 85.0% yield, S-BINOL was in 83.1% yield. The results exceeded the date of literature.The Optical purity of R-BINOL, S-BINOL is>99%. The recovery of N-benzyl-cinchoninium is about 90% and can be used in a circle.(2) resolution of BINOL using L-prolineThe R-BINOL was gained in 35.2%yield, S-BINOL was in 45.3% yield. The Optical purity of R-BINOL, S-BINOL is>99%.When ethyl acetate, butyl acetate and other reagents replace acetonitrile as optical resolution reagents, it can gain R-BINOL with>99%.The results have not been reported; The aprotic solvent sorts of methanol and the other reagents were used and can gain R-BINOL with> 99%. This result hasn’t been reported by any literature.In the fourth part, a new synthesis method of the chiral internal electron donor R-2,2’-dimethoxy-1,1’-binaphthyl and S-2,2’-dimethoxy-1,1’-binaphthyl has been developed. At room temperature for 0.5h, the conversion rate of the chiral 2,2’-dihydroxy-1,1’-binaphthyl and dimethyl sulfate was 99%, the purity of chiral 2,2’-dimethoxy-1,1’-binaphthyl is 98.5%.