14-Bromotetradecanol

Synthesis Example D-(25) 1, 14-Tetradecandiol (1.5 g) was dissolved in 16.5 ml of cyclohexane, and 57percent aqueous hydrobromic acid solution (16.5 ml) was added to this solution. The reaction mixture was refluxed for six hours while stirring. After the reaction, the mixture was extracted three times with diethyl ether. The organic layer was neutralized with saturated sodium hydrogen carbonate solution, washed with saline solution, dried over magnesium sulfate, and filtered, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel flash chromatography (hexane: ethyl acetate = 7:3) gave 14-bromotetradecan-1-ol as white crystals at a 67percent yield. Molecular weight: 292.90 (CA mixture of 14-Bromo-1-tetradecanol (10.00 g, 34.1 mmol) was dissolved in 6 dichloromethane (34.1 mL), and 7 imidazole (5.11 g, 75.0 mmol) was added to the solution. 8 TIPSCl (7.95 mL, 37.5 mmol) was dropwise added to the mixture, followed by stirring at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was dissolved in 11 heptane (136 mL), followed by liquid-liquid extraction with water (34 mL) once, 1 N 9 hydrochloric acid (34 mL) once, 10 water (34 mL) twice, and 39 acetonitrile (34 mL) once. Heptane (34 mL) was added to the resulting heptane layer, followed by liquid-liquid extraction with acetonitrile (34 mL). The liquid-liquid extraction with heptane and acetonitrile was further repeated once, and the heptane layer was then concentrated under reduced pressure to obtain 92 Br-(CH2)14-O-TIPS (15.41 g). (0161) 1H-NMR (400 MHz, CDCl3) delta 1.04-1.08 (m, 21H), 1.24-1.38 (m, 18H), 1.42 (quin., 2H), 1.53 (quin., 2H), 1.85 (quin., 2H), 3.40 (t, 2H), 3.67 (t, 2H)

Molecular Weight:293.28
XLogP3:6.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:13
Exact Mass:292.14018
Monoisotopic Mass:292.14018
Topological Polar Surface Area:20.2
Heavy Atom Count:16
Complexity:117
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes