Cyclododecanol → Cyclododecane, propoxy-

Participants

Reaction Steps

Cyclododecanol (2.6 g, 14.11 mmol), 1-iodopropane (1.74 g, 102.54 mmol), and 60% sodium hydride in mineral oil (750.0 mg, 18.75 mmol) prepared as in Example 1 were strongly refluxed for 3 hours. A 3.0 g sample (94.0%) was isolated as in Example 1. GC showed 99% one component; bp 69°-71° C. at 0.09 mm. IR (neat, cm-1) 2955, 2882, 1485, 1460, 1350, 1105 (C-O-C); 13C NMR (ppm, CDC13) 77.02 (α-ring carbon), 70.32 (α-chain carbon), 29.18, 24.94, 24.49, 23.39, 20.98, 10.82. Anal calcd for C15H30O:C,79.58, H,13.36. Found: C,79.55; H,13.42.

Provenance & Evidence