Study On The Synthesis Of Deoxyarbutin

4-[(Tetrahydro-2H-pyran-2-yl)oxy]phenol (Deoxyarbutin) is a new and effective tyrosinase inhibitor which could be used as cosmetic additive to achieve skin lightening. Compared with the present popular tyrosinase inhibitors such as arbutin hydroquinone, white effect of deoxyarbutin is much better. And the damage caused by deoxyarbutin to melanophore is not permanent, therefore, the composition of melanophore could be recovered to a normal level after stopping using it for a period of time.This study focuses on an improved synthetic route of 4-[(tetrahydro-2H-pyran-2-yl)oxy]phenol and its optimization conditions on the basis of the proposed route reported by precusors. The improved synthetic route was designed with the single phenolic hydroxyl condensation for the preparation of p-benzyloxyphenol starting from hydroquinone and benzyl chloride followed by the reaction with 3,4-dihydropyran to afford 2-[4-(benzyloxy) phenoxy] tetrahydropyran. Eventually,4-[(2-tetrahydropyran)oxy]phenol was prepared by hydrogenation to rid the benzyl off. And the use of different alkaline sorbents was also studied for the purpose of controlling the concentration of hydroquinone.Appropriate reaction conditions were obtained by studying the influence of several factors on the yield in terms of reaction temperature, amount of catalyst and rate of charge. A 75% yield was obtained by the 1.5 hour reaction of hydroquinone with benzyl chloride at 64.5℃in the sodium hydroxide, methanol system. A 80% yield was obtained by the etherification of the other phenolic hydroxyl group with 3,4-dihydropyran at 30℃for 5 hours using dichloromethane as solvent and pyridine p-toluenesulfonate salt as a catalyst. And a 79% yield of 4-[(2-tetrahydropyran)oxy]phenol was obtained by hydrogenation of 2-[4-(benzyloxy)phenoxy]tetrahydropyran to rid of the benzyl at 30℃for 24 hours using ethyl acetate as solvent, palladium as catalyst and sodium carbonate as absorbent.The content of hydroquinone in the product was lower than 100 ppm. The melting point of the product obtained was found to be the conformity of those reported in literatures. The purity of the title compound was analized by HPLC, and its structure was confirmed by 1H-NMR. And also, pilot process and cost accounting were studied. The results proved that this process is feasible in production. This proposed synthetic process is much of industrial value because of the high yield, easily available and cheap materials, the moderate reaction conditions and the convenient operation.