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ChemicalBook CAS DataBase List 2,5-DIMETHOXYBENZYL ALCOHOL
33524-31-1

2,5-DIMETHOXYBENZYL ALCOHOL synthesis

6synthesis methods
2,5-Dimethoxybenzaldehyde

93-02-7

2,5-DIMETHOXYBENZYL ALCOHOL

33524-31-1

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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Yield:-

Steps:

Multi-step reaction with 2 steps
1: titanium tetrachloride / dichloromethane / 1.5 h / -5 - 20 °C / Inert atmosphere
2: sodium tetrahydroborate / methanol / 3 h / -10 °C

References:

CN112321413, 2021, A

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