Sodium Iodide → 3-(2-Naphthalenylmethoxy)-α-pentylbenzenemethanol

Participants

Reaction Steps

A suspension of 2-bromomethyl naphthalene (5 g, 0.023 mol), 3-(1-hydroxyhexyl)phenol (5 g, 0.026 mol), powdered potassium carbonate (4.5 g, 0.033 mol), sodium iodide (0.4 g, 0.0023 mol) and cesium carbonate (0.7 g, 0.0021 mol) in dry acetone (75 ml) was refluxed overnight (14 hours). The reaction mixture was filtered, the filtrate was concentrated, dissolved in ether, and then washed successively with 1N NaOH solution 6N HCl solution, water and brine. After drying the organics over anhydrous MgSO4, all volatiles were removed. The crude product (5 g) was further purified by chromatography, using 8% ethylacetate in hexanes on silica gel, to yield 3.5 g of the pure desined compound as a colorless liquid.

Provenance & Evidence