1-Bromohexane → n-Hexyloxycyclododecane

HRID 36469

Reaction equation

[CH:1]1([OH:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[H-].[Na+]>>[CH2:15]([O:13][CH:1]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

Reactant 3

HCID 81011-Bromohexane

HCID 15595Cyclododecanol

HCID 24758Sodium hydride

Product 1

HCID 19938744n-Hexyloxycyclododecane

Procedure

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.

Workup

temperaturewere refluxed for 2 hours
customA 28.4 g sample (96%) was isolated as in Example 1

Sources & evidence

ORD record: ord-363883e4eeab44bd95dacee5538f764e
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05414142

Linked notes

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