Hydrochloric Acid → 2-Methoxy-6-dodecanoylnaphthalene

Participants

Reaction Conditions

Reaction Steps

2-Methoxynaphthalene (30.1 g, 0.19 mol) was added to a solution of aluminum chloride (32.9 g, 0.25 mol) in anhydrous nitrobenzene under a nitrogen atmosphere. To the mixture was slowly added dropwise lauryl chloride (41.6 g, 0.19 mol) at 10-13° C. over 15 minutes. The resulting mixture was stirred at 5° C. for 2 hours and at room temperature for 12 hours. The reaction mixture was poured into 300 ml of 3M HCl at 0° C., extracted with chloroform, and sufficiently washed with brine. The solvents were removed by evaporation under reduced pressure. The residue was dissolved in chloroform and washed with 0.1M NaOH. The mixture was evaporated to remove the chloroform, followed by recrystallization from ethanol to give the title compound (41.5 g, yield: 64.2%).

Provenance & Evidence