Dimethylamine → 1-(6-(Dimethylamino)-2-naphthalenyl)-1-dodecanone

Participants

Reaction Steps

Li (0.5 g, 70 mmol) was added to HMPA (20 ml) and benzene (30 ml), and then dimethylamine (3.5 g, 78 mmol) was added dropwise thereto. The mixture was violently stirred for one hour. To the resulting mixture was added 2-methoxy-6-dodecanoylnaphthalene (7.3 g, 22 mmol) prepared in Comparative Example 1-(1) all at one time. The mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into ice-water, extracted with ether, evaporated to remove the solvents, and recrystallized from ethanol to give Laurdan (5.1 g, yield: 66%).

Provenance & Evidence