合成路线1

The synthesis of 3,4-bis(3'-methoxyphenyl)hexane (III) was accomplished in two different ways: 1) Reductive coupling of the 3-methoxypropiophenone (I) using the TiCl4/Zn reaction -- introduced by Mukaiyama et al. -- yields preferably the cis-stilbene (II). Catalytic hydrogenation of this alkene using palladium on activated carbon results in the isomerically pure meso-3,4-bis(3'-methoxyphenyl)hexane (III). 2) The reductive coupling of the 1-(3'-methoxyphenyl)-1-chloropropane (VI), obtained from 1-(3-methoxyphenyl)propanol (V) with dry HCl, according to Wilds and McCormack using COCl2 and ethylmagnesium bromide (A) yields mixture of the meso- and di-3,4-bis(3'-methoxyphenyl)hexanes (III). The meso-diastereomer (III) is separated by fractional crystallization from methanol. The ether cleavage of (III) to give 3,4-bis(3'-hydroxyphenyl)hexane is accomplished with BBr3.