Tetrahydrofuran → (2-Methyl-1,4-phenylene)dimethanol

Participants

Reaction Steps

A 200 ml round-bottomed flask was charged with 1 g (25 mmol) of lithium aluminum hydride, and under an argon atmosphere, 50 ml of anhydrous tetrahydrofuran was added. While the resultant mixture was stirred, 50 ml of an anhydrous tetrahydrofuran solution of 2.8 g (19 mmol) of 2-methylterephthalaldehyde was added through a dropping funnel over 20 minutes. The resultant mixture was heat-refluxed for 2 hours, and while the reaction mixture was hot, 1 ml of water, 1 ml of a 50% sodium hydroxide aqueous solution and 3 ml of water were consecutively added in this order. A white precipitate formed was separated by filtering, and the tetrahydrofuran solution was dried over magnesium sulfate, followed by distilling the solvent off with a rotary evaporator and drying under reduced pressure, whereby 2.7 g (18 mmol) of 2,5-bis(hydroxymethyl)toluene was obtained (yield 95%).

Provenance & Evidence