Chemical Properties
clear colorless to light yellow viscous liquid
Uses
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.
Uses
2,5-Dimethoxybenzyl Alcohol can be used as a self-indicating standard for the determination of organolithium reagents
Synthesis
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).
References
[1] Journal of Organic Chemistry, 2007, vol. 72, # 24, p. 9190 - 9194
[2] Organic and Biomolecular Chemistry, 2010, vol. 8, # 17, p. 3965 - 3974
[3] Tetrahedron Letters, 2011, vol. 52, # 9, p. 983 - 986
[4] European Journal of Organic Chemistry, 2011, # 27, p. 5331 - 5335
[5] Green Chemistry, 2017, vol. 19, # 14, p. 3296 - 3301
