Sodium Iodide → 1-(2-Methoxyethoxy)naphthalene

Participants

Reaction Conditions

Reaction Steps

In 100 g of ethanol were dissolved 50.0 g (0.347 mol) of 1-naphthol, 34.4 g (0.364 mol) of 2-methoxyethyl chloride, 14.6 g (0.365 mol) of sodium hydroxide, and 2.6 g (0.017 mol) of sodium iodide. The solution was heated and stirred at 80° C. for 8 hours. After cooling, the solution was combined with 100 g of water and 200 g of toluene, from which an organic layer was separated. It was washed 5 times with 100 g of 5 wt % sodium hydroxide aqueous solution and then 4 times with 100 g of water. The organic layer was concentrated, obtaining 45 g of oily matter. On vacuum distillation (110° C./13 Pa), 41 g of the target compound was recovered (yield 58%).

Provenance & Evidence