2-(methoxymethoxy)naphthalene

Conditions: temp:80.01; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 5.0 g of NaH (208.33 mmol) in 150 mL of DMF under argon flow were added 20.0 g of solid 2-hydroxynaphthalene (138.7 mmol) at a temperature of 0° C., by small portions. The suspension was kept under stirring for 4 h at room temperature, 17.8 g of methoxymethyl chloride (221.2 mmol) were added slowly, and the reaction mixture was stirred for 10 additional hours. The reaction was carefully diluted with 1 L of water and the organic part was extracted with 3 times 50 mL of CH2Cl2. The combined organic extracts were washed twice with 500 mL of water, brine and dried over MgSO4. The solution was evaporated, dried in vacuum at a temperature of 80° C. to give 25.1 g of colorless oily product (133.3 mmol) that was used without further purification. the reaction mixture was stirred for 10 additional hours the organic part was extracted with 3 times 50 mL of CH2Cl2 The combined organic extracts were washed twice with 500 mL of water, brine dried over MgSO4 The solution was evaporated dried in vacuum at a temperature of 80° C.