SYNTHESIS OF BINAPHTHOL-DERIVED PODANDS BASED ON SELECTIVE, ACID-PROMOTED REACTION OF BENZYLIC ALCOHOLS WITH ETHYLENE GLYCOLS

3-Hydroxymethyl and 3,3'-bis(hydroxymethyl) binaphthols (1,2) react un der acidic conditions smoothly with ethylene glycols to afford corresp onding ethers 3 and 4, mostly in good to excellent yields. Screening e xperiments revealed that the reaction occurs efficiently with several different Lewis acids. Glycerine as glycol component, gives a 7:1 mixt ure of 1 degrees-OH- and 2 degrees-OH-derived products 5 and 6. Monoal kyl derivatives of ethylene glycols are behaving in a similar way the reaction times being substantially longer.