1-Bromopentane → 2-(1-Pentoxyethyl)furan

Participants

Reaction Steps

Ten grams of the distilled 1-furylethanol (0.089 mole) is charged to a reactor with 0.61 g (2 mole percent) tetrabutylammonium bisulfate and 19.2 g of a 50 percent aqueous solution of sodium hydroxide added over a 15 minute period with stirring. This is followed by addition of 34.7 g (0.25 mole) 1-bromopentane over a period of 15 minutes and the reaction mixture allowed to stir for 3 hours. The reaction mixture is then extracted with diethyl ether which, after drying over magnesium sulfate, is evaporated. The resulting crude product is short-path distilled to obtain 2-(1-pentoxyethyl)furan in low yield (B.p. 35° C. at 0.2 mm Hg.). The structure of the 2-(1-pentoxyethyl)furan ##STR5## is confirmed by infrared and nuclear magnetic resonance spectroscopy.

Provenance & Evidence