The O-alkylation of S(-)-1

1’-bis-2-naphthol [S(-)-1]

or R(+)-1 with various alkyl halides in the presence of potassium fluoride hydrate was studied. It was found that mono-alkyl ether (3) was the major product

when S-1 or R-1 reacted with aliphatic monobromide or iodde in DMF at 100℃ under neutral reaction conditions. A good to exceillent yield of 3 was obtained when primary or secondary alkyl halide was used. No racemization was determined by the method of either optical rotation or proton nuclear magnetic resonance with chiral shift reagent. This synthetic method was also extended to methylene dihalide. When it reacted with S-1

for example

a cyclic ether S-5 was obtained in the yield of 84%.