2,5-Dimethoxybenzyl alcohol was used as starting reagent in the synthesis of [(S)S]-3,6-dimethoxy-2-(p-tolylsulfinyl)-benzaldehyde. It was used in the synthesis of daunornycinone. It was also used in the preparation of pillar[n]arenes (n = 5 or 6) via cyclooligomerization reaction with an appropriate Lewis acid catalyst.
General procedure for the synthesis of p-dimethoxybenzyl alcohol from 2,5-dimethoxybenzaldehyde: A solution of 2,5-dimethoxybenzaldehyde (3.32 g, 20 mmol) in THF (20 mL) was slowly added to a suspension of LiAlH4 (748 mg, 22 mmol) in THF (20 mL) at 0 °C. The reaction mixture was stirred at 0 °C for 30 min. Subsequently, the reaction was carefully quenched with saturated Na2SO4 solution (10 mL) at 0 °C and the resulting suspension was stirred for 3 hours. The reaction mixture was filtered through a silica gel pad and the filtrate was dried with Na2SO4. After evaporation of the solvent under reduced pressure, the residue was purified by column chromatography (petroleum ether-EtOAc, 1:1) to afford p-dimethoxybenzenemethanol as a colorless, thick liquid (3.06 g, 91%). rf = 0.4 (petroleum ether-EtOAc, 1:1).
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