Boron trifluoride etherate → 1,1'-Binaphthalene, 4,4'-dimethoxy-

Participants

Reaction Steps

In synthetic route `A3`, 1-methoxynaphthalene and a solution of tris(trifluoroacetato)thallium[III] in acetonitrile are charged to a reaction vessel. Boron trifluoride etherate is added and the reaction mixture stirred at room temperature for between approximately 1-2 h to provide the intermediate 4,4'-dimethoxy-1,1'-binaphthyl. The 4,4'-dimethoxy-1,1'-binaphthyl intermediate is subsequently demethylated using boron tribromide (BBr3) which is added slowly to a dichloromethane solution of the intermediate to maintain the temperature at about -78° C. The reaction mixture is then warmed to room temperature and stirred for approximately 16 h in an inert atmosphere, then poured into water. The white crystals that form are 4,4'-Dihydroxy-1,1'-binaphthyl.

Provenance & Evidence