Dimethyl Sulfoxide → HCID 22222982, compound

Participants

Reaction Steps

A 500 mL round bottom flask equipped with a mechanical stirrer was charged with 33.6g (0.30 mol) cyclohexene-1-methanol, and 260 mL of DMSO. Sodium hydride (8.43 g, 95% in purity; 0.334 mol) was slowly added to above mixture in ice bath over 40 min. After the above mixture was reacted at room temperature for 2 hrs, the reaction mixture was warmed to room temperature. 2-Ethylhexyl tosylate (85.2 g, 0.30 mol) was slowly added to the above mixture over 15 min. The reaction was carried out for another 1 hr at room temperature, then 60° C. for 2 hrs. The reaction mixture was added to water (200 mL), and then extracted with chloroform (3×180 mL), washed with water (2×100 mL). The organic layer was evaporated and the residue distilled to give pure product.

Provenance & Evidence