Methyl 3,5-bis(methoxymethoxy)benzoate → 3,5-Bis(methoxymethoxy)benzylalcohol

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,5-bis-methoxymethoxy-benzoic acid methyl ester (220a) (350 g, 1.37 mol) in THF (1.8 L) was added portion wise LiAlH4 (62 g, 1.64 mol) at 0° C. The mixture was stirred at 0° C. for another 1 hr. TLC (EtOAc/petroleum ether=1/2) showed that the reaction was complete. The reaction was quenched with 2 N aqueous NaOH. The mixture was filtered through Celite. The filtrate was dried over Na2SO4 and concentrated to give the title compound (290 g, 76%) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 6.70 (d, 2H), 6.64 (d, 1H), 5.22 (s, 4H), 4.61 (s, 2H), 3.46 (s, 6H).

Provenance & Evidence