Methanol → HCID 590599, compound

Participants

Reaction Steps

Under an argon atmosphere, a 500 ml round-bottomed flask was charged with 140 ml of a toluene solution of 4.6 g (33 mmol) of the diethyl 2-methylterephthalonitrile, and further, 87 ml of a toluene solution of 18.6 g (131 mmol) of diisobutylaluminum hydride was added dropwise at -78° C. The resultant mixture was stirred for 30 minutes as it was, and then allowed to further react at room temperature for 5 hours. While the reaction mixture was hot, 4 ml of methanol was added to decompose an excess amount of the diisobutylaluminum hydride. Thereafter, the reaction mixture was poured into 250 ml of a saturated ammonium chloride aqueous solution, and the resultant mixture was stirred at room temperature for 20 minutes. The reaction mixture was recharged into a separating funnel, 100 ml of 10% sulfuric acid was added, and the resultant mixture was shaken vigorously. And, an organic layer formed was separated. This organic layer was washed with sodium bicarbonate and salt water, and dried over magnesium sulfate. The solvent was distilled off with a rotary evaporator, and the residue was purified by column chromatography to give 2.8 g (19 mmol) of 2-methylterephthalaldehyde.

Provenance & Evidence