ChemicalBook CAS DataBase List 16-Bromohexadecanol

16-Bromohexadecanol synthesis

10synthesis methods

Product Name:16-Bromohexadecanol
CAS Number:59101-28-9
Molecular formula:C16H33BrO
Molecular Weight:321.34

7735-42-4 Synthesis

7735-42-4
130 suppliers
$45.00/10mg

59101-28-9
106 suppliers
$99.70/500mg

Yield: 96%

Reaction Conditions:

with hydrogen bromide in cyclohexane for 6 h;Reflux;

Steps:

4.2 4.2 16-Bromohexadecan-1-ol
4.2 1 6-Bromohexadecan- 1 -ol10215] The diol 14 (1.047 g, 4.05 mmol) was dissolved in cyclohexane (30 mE) and vigorously stirred with 48% HBr (0.5 mE, 4.46 mmol, 1.1 eq.). The mixture was refluxed for 6 h, diluted with water (50 mE) and the phases were separated. The aqueous phase was extracted with a mixture of dichloromethane and methanol (v/v, 4:1 3x20 mE). The combined organic layer was dried over Mg504. The product was purified by column chromatography with silica gel (6x6 cm, cyclohexane/ethyl acetate, 8:1) and isolated as a white solid. Yield: 4.598 g (96%). Traces of i,i6-dibromohexadecane were also found.1515 13 11 9 7 5 3 1j0216] M.p.: 65° C. (lit. 53-54° C.)j0217] ‘H-NMR (300 MHz, CDC13) ö [ppm]: 1.26-1.47 (m, 23H, 4-CH2 to i4-CH2, i-OH), 1.51-1.62 (m, 4H, 2-CH2, 3-CH2), 1.85 (m, 2H, i5-CH2), 3.41 (t, 3JH,H=6.9 Hz, 2H, i6-CH2), 3.64 (t, 3J,y=6.6 Hz, 2H, i-CH2).10218] ‘3C-NMR (75 MHz, CDC13) ö [ppm]: 25.9 (t, C-3),28.3, 28.9, 29.6, 29.7, 29.8 (t, C-4 to C-i4), 33.0 (t, C-2, C-iS), 34.3 (t, C-i6), 63.3 (t, C-i).10219] Refs.: M.p. P. Chuit, J. Hausser, Helv. Chim. Acta1929, 12, 850-859.10220] ‘H-NMR spectroscopic data agree with those given by: S. Takanashi, M. Takagi, H. Takikawa; K. Mori, I Chem. Soc., Perkin Trans. 11998, 1603-1606.

References:

WESTFAELISCHE WILHELMS-UNIVERSITAET MUENSTER;Haufe, Guenter;Levkau, Bodo;Schaefers, Michael;Schilson, Stefani Silke;Keul, Petra US2014/170067, 2014, A1 Location in patent:Paragraph 0215; 0216; 0217; 0218; 0219; 0220

2536-35-8 Synthesis