14. 超音波照射を用いた置換フェノール類のアルコキシ及びエステル合成

概要

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Various phenols substituted with methyl and methoxy groups were reacted with silica gel (230-400 mesh) and aluminium trichroride under ultrasonic irradiation(Sus-4005C, 50W, 40kHz) for 30 min-1h to give the corresponding alkoxy compounds in good yields. Trimethylhydroquinone in various alcohols was treated under ultrasonic irradiation with anhydrous aluminium trichloride for 30 min to give the corresponding 4-alkoxy-2,3,6- trimethylphenol in high yield. Using t-butanol as solvent, only the starting material was recopvered. From these result, the reaction mechanisms are thought as follows. The intermediary aluminium alkoxides were attacked by trimethylhydroquinone to produce the alkoxy phenols. The bulky aluminium alkoxides produced from sterically hindered alcohols were difficult to be attacked by trimethylhydroquinone, which is seen in the yields of the case of t-BuOH, i-AmOH and i-PrOH.[table]
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