Reaction #70121

Reaction equation

1-naphthol

2-methoxyethyl chloride

sodium hydroxide

sodium iodide

→

1-(2-methoxyethoxy)naphthalene

Yield 58.0%

Solvents

toluene

water

ethanol

Conditions

Workup

1. 1
   TemperatureThe solution was heated
2. 2
   TemperatureAfter cooling
3. 3
   Otherwas separated
4. 4
   WashIt was washed 5 times with 100 g of 5 wt % sodium hydroxide aqueous solution
5. 5
   ConcentrationThe organic layer was concentrated
6. 6
   Otherobtaining 45 g of oily matter
7. 7
   workup.DISTILLATIONOn vacuum distillation (110° C./13 Pa), 41 g of the target compound
8. 8
   Otherwas recovered (yield 58%)

Procedure

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%).

Source