Paper
Synthesis of 4-[(Tetrahydro-2H-pyran-2-yl)oxy] phenol
Published 2010 · Chen Ying-qi
Journal of Chemical Engineering of Chinese Universities
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Abstract
4-[(Tetrahydro-2U-pyran-2-yl)oxy]phenol is an effective tyrosinase inhibitor, which could be used as cosmetic additive to achieve lightening skin. A synthetic rout of 4-[(Tetrahydro-2U-pyran-2-yl)oxy]phenol was designed by using hydroquinone as raw material and via hydroquinone monobenzyl etherification, another phenolic hydroxyl tetrahydropyran etherification and debenzylation by catalytic hydrogenation. Comparing with methods reported in literatures, the second step can get a good result with PPTS as catalyst. The suitable reaction conditions (temperature, time and molar yield) of the proposed rout were found as follows: 75℃, 3 h and 36% for hydroquinone monobenzyl etherification; 30℃, 5 h and 80% for another phenolic hydroxyl tetrahydropyran etherification; 30℃, 24 h and 79% for hydrotreating debenzylimine. The melting point of the obtained product was found to be in conformity with those reported in literatures, and the structure of the title compound was confirmed by 1H-NMR.
The synthetic route for 4-[(Tetrahydro-2U-pyran-2-yl)oxy]phenol, an effective tyrosinase inhibitor, can be optimized for cosmetic applications, with PPTS as catalyst.
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