Reaktion #64747

Reaktionsgleichung

Cyclododecanol

1-bromohexane

sodium hydride

→

n-Hexyloxycyclododecane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwere refluxed for 2 hours
2. 2
   SonstigeA 28.4 g sample (96%) was isolated as in Example 1

Vorschrift

Cyclododecanol (20.0 g, 0.11 tool), 1-bromohexane (120.0 g, 0.727 mol), and 60% sodium hydride in mineral oil (5.6 g, 0.14 mol) prepared as in Example 1 were refluxed for 2 hours. A 28.4 g sample (96%) was isolated as in Example 1. GC showed 99% one component; bp 109°-111° C. at 0.03 min. IR (neat, cm-1) 28 38, 2868, 1470, 1452, 1354, 1100 (C-O-C); 13C NMR (ppm, CDC13) 76.90 (α-ring carbon), 68.64 (α-chain carbon), 31.81, 30.31, 2 9.06, 26.00, 24.78, 24.31, 23.29, 22.71, 20.78, 14.10; MS, m/z (relative intensity) 268 (M+,1.1), 225(0.03), 211(0.2), 197(1.0), 183(0.4), 138(2.4), 124(3.6), 111(4.5), 110(6.4), 97(2.0), 96(19.9), 83(15.4), 82(46.5), 69(16.1), 68(17.1), 55(34.2), 54(6.2), 43(100.0), 41(40.3), 39(14.8). Anal calcd for C18H36O:C,80.53; H,13.52. Found: C, 80.77; H, 13.33.

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