With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.7735-42-4, name is 1,16-Hexadecanediol, molecular formula is C16H34O2, molecular weight is 258.44, as common compound, the synthetic route is as follows.category: alcohols-buliding-blocks
The diol 14 (1 .047 g, 4.05 mmol) was dissolved in cyclohexane (30 mL) and vigorously stirred with 48% HBr (0.5 mL, 4.46 mmol, 1.1 eq.). The mixture was refluxed for 6 h, diluted with water (50 mL) and the phases were separated. The aqueous phase was extracted with a mixture of dichloromethane and methanol (v/v, 4:1 3 x 20 mL). The combined organic layer was dried over MgS04. The product was purified by column chromatography with silica gel (6 x 6 cm, cyclohexane/ethyl acetate, 8:1 ) and isolated as a white solid. Yield: 4.598 g (96%). Traces of 1 ,16-dibromohexadecane were also found. 15 M.p.: 65 C (lit. 53-54 C) 1H-NMR (300 MHz, CDCI3) delta [ppm]: 1.26-1.47 (m, 23 H, 4-CH2 to 14-CH2, 1 -OH), 1.51 -1.62 (m, 4 H, 2-CH2, 3-CH2), 1 .85 (m, 2 H, 15-CH2), 3.41 (t, 3JH,H = 6.9 Hz, 2 H, 16-CH2), 3.64 (t, 3JH,H = 6.6 HZ, 2 H, 1 -CH2). 13C-NMR (75 MHz, CDCI3) delta [ppm]: 25.9 (t, C-3), 28.3, 28.9, 29.6, 29.7, 29.8 (t, C-4 to C-14), 33.0 (t, C-2, C-15), 34.3 (t, C-16), 63.3 (t, C-1 ). Refs.: M.p. P. Chuit, J. Hausser, Helv. Chim. Acta 1929, 72,850-859. 1H-NMR spectroscopic data agree with those given by: S. Takanashi, M. Takagi, H. Takikawa; K. Mori, J. Chem. Soc, Perkin Trans. 1 1998, 1603-1606.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,7735-42-4, 1,16-Hexadecanediol, and friends who are interested can also refer to it.
Reference:
Patent; WESTFAELISCHE WILHELMS-UNIVERSITAET MUENSTER; HAUFE, Guenter; LEVKAU, Bodo; SCHAEFERS, Michael; SCHILSON, Stefani Silke; KEUL, Petra; WO2013/26765; (2013); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts