Ethanol → 2-(2-Aminoethoxy)naphthalene

Participants

Reaction Conditions

Reaction Steps

A 3-neck round bottom flask was charged with water (50 mL) and barium hydroxide (12.27 g, 71.61 mmol) while stirring. The resulting slurry was charged with ethanol (50 mL) and finally N-(2-(naphthalen-2-yloxy)ethyl)acetamide (10.0 g, 35.80 mmol) as prepared above. The resulting mixture was heated to reflux for 18 h. The reaction was monitored by TLC. The reaction was then allowed to cool to 50° C., then charged with water (50 mL) followed by ethyl acetate (100 mL). The mixture was then stirred for 15 min. The mixture was then filtered and thelayers were separated. The upper organic layer was washed with saturated sodium chloride (50 mL) and dried over sodium sulfate and concentrate to afford 2-(2-naphthyloxy)ethylamine as an amber oil (6.92 g, 47%).

Provenance & Evidence