1-Butanol → Butyl Oleyl Ether

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Reaction Steps

Sodium (2.33 g, 0.10 mol) was placed in a three-necked, 250-mL round-bottom flask equipped with nitrogen inlet, mechanical stirrer and drying tube, and 1-butanol (36.6 mL, 0.4 mol) was added to the flask. The reaction mixture was left in a hood overnight, by which time evolution of hydrogen had ceased and all of the sodium appeared to have reacted. Oleyl tosylate (17 g, 0.04 mol, made from oleyl alcohol and tosyl chloride) dissolved in 1-butanol (9.15 mL, 0.1 mol) was added. The solution, which began to turn yellow immediately, was packed in ice and allowed to warm to room temperature over 15 hr. The reaction mixture was washed with water. The organic phase was dissolved in ether and extracted with 10% Na2CO3 and with saturated NaCl. The ether phase was dried over anhydrous potassium carbonate and filtered, and the solvent was removed on a rotary evaporator. The resulting pale-orange oil was distilled (155-168° C. at 0.6 torr) to yield 8.2 g (64%) of 2 as an oil: NMR δ 0.9-2.2 (m, 38 H, --CH3 and --CH2 --), 3.2 (t, J=6 Hz, 4 H, --CH2 --O), 5.28 (t, J=4.5 Hz, 2 H, olefinic); IR:3010 (olefinic C--H), 1120 cm-1 (C--O). Anal. Calcd.: C, 81,41; H, 13.66. Found: C, 81.44; H, 13.68.

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