1-Naphthol → 2-((1-Naphthalenyloxy)methyl)oxirane

Participants

Reaction Steps

To a solution of 1-naphthol (3.0 g, 0.02 mol) in DMSO (10 mL), potassium hydroxy (flakes, 2.0 g, 0.06 mol) was added. The combined mixture was stirred at room temperature for 30 min and then epichlorohydrin (5.6 g, 4.7 mL, 0.06 mol) was added slowly over a period of 45 min and stirring was continued for 16 hours. The reaction was quenched with water (30 mL) and extracted with chloroform (2×50 mL). The combined organic layers were washed with 1N aqueous NaOH (2×50 mL), water (2×100 mL) and brine (2×100 mL) and dried over MgSO4. The solvent was removed under reduced pressure to provide Compound 1 as a yellow liquid (3.26 g, 78%). This product was used without further purification. The structure of Compound 1 is given below:

Provenance & Evidence