Benzaldehyde → HCID 19026968, compound

Participants

Reaction Steps

To a solution of 2-methoxymethoxy-5-methylaniline (see Example 8) (15.6 g, 93.3 mmol), ethanol (100 ml), acetic acid (75 ml), benzaldehyde (19.0 ml, 187 mmol) and sodium acetate (15.5 g, 189 mmol) was added sodium borohydride (7.15 g, 189 mmol) under ice-cooling over a period of 30 minutes. The reaction mixture was stirred at 0° C. to room temperature for 1 hour. The reaction mixture was poured into 1N sodium hydroxide (500 ml) and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The crude product was purified by column chromatography on silica gel to give white crystals. The crystals were recrystallized from chloroform/hexane to give the desired benzylaniline compound (1). Yield 25.2 g (86%, a mixture with dibenzyl compound in the ratio of 6:1).

Provenance & Evidence