Category: 14722-40-8

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 14722-40-8, name is Pentadecane-1,15-diol, the common compound, a new synthetic route is introduced below. Application In Synthesis of Pentadecane-1,15-diol

General procedure: Under an atmosphere of N2, a 97% H3PO4 solution (8.7 equiv) was prepared by adding P2O5 (300 mg, 2.10 mmol, 1.4 equiv) to 85% H3PO4 (0.6 mL, 0.85 g H3PO4, 8.67 mmol, 5.8 equiv). To this solution was added KI (1.44 g, 8.70 mmol) and then 1,15-pentadecanediol (367 mg, 1.50 mmol, 1 equiv). The reaction mixture was stirred at ?115 C for 4 h, cooled to rt, diluted with Et2O (20 mL), and water (20 mL) was added. The organic layer was separated, and the aqueous phase extracted with an additional 50 mL of Et2O. The combined organic extracts were washed with brine (20 mL), washed with a concentrated aqueous solution of Na2S2O3 (10 mL), dried (Na2SO4), and then concentrated. High-vacuum drying gave 1,15-diiodopentadecane (683 mg, 1.47 mmol, 70%) as a white solid;

The synthetic route of 14722-40-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vlahakis, Jason Z.; Mitu, Simona; Roman, Gheorghe; Rodriguez, E. Patricia; Crandall, Ian E.; Szarek, Walter A.; Bioorganic and Medicinal Chemistry; vol. 19; 21; (2011); p. 6525 – 6542;,
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Related Products of 14722-40-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 14722-40-8 as follows.

Compound 9 (204.9 mg, 0.379 mmol) was dissolved in CH2Cl2 (4 mL) and Ph3P (294.9 mg, 1.12 mmol), CBr4 (374.3 mg, 1.13 mmol) was added. After stirring for 4 h, THF (4 mL) solution of TMU (272 muL, 2.27 mmol), 15-hydroxypentadecanol (180.6 mg, 0.74 mmol), and TEAB (95.7 mg, 0.455 mmol) was added and further stirred for 12 h. The reaction mixture was diluted with 1 M HCl aq and extracted by EtOAc. The organic layer was washed with satd NaHCO3 aq and brine, dried over sodium sulfate, evaporated and purified by silica-gel column chromatography (hexane/EtOAc=9/1 to 3/1) to give 14 (123.6 mg, 43%) as an oil.Comment1H NMR (500 MHz, CDCl3, rt): 7.36-7.22 (18H, m), 7.15-7.12 (2H, m), 4.99 (1H, d, J=10.8 Hz), 4.83 (1H, d, J=10.8 Hz), 4.81 (1H, d, J=10.8 Hz), 4.76 (1H, d, J=12.1 Hz), 4.76 (1H, d, J=3.7 Hz), 4.64 (1H, d, J=12.1 Hz), 4.59 (1H, d, J=12.1 Hz), 4.47 (1H, d, J=10.8 Hz), 4.45 (1H, d, J=12.1 Hz), 4.00 (1H, dd, J=9.2, 9.2 Hz), 3.79 (1H, ddd, J=1.9, 3.6, 9.9 Hz), 3.72 (1H, dd, J=3.6, 10.7 Hz), 3.66-3.60 (3H, m), 3.56 (1H, dd, J=3.7, 9.2 Hz), 3.55 (2H, t, J=6.7 Hz), 3.42 (1H, dt, J=9.8, 6.7 Hz), 1.63 (2H, tt, J=6.7, 7.0 Hz), 1.51 (2H, tt, J=6.7, 6.7 Hz), 1.38-1.24 (22H, m) ppm; 13C NMR (125 MHz, CDCl3, rt): 138.8, 138.2, 138.1, 137.8, 128.2, 128.1, 127.8, 127.72, 127.69, 127.6, 127.5, 127.3, 96.7, 81.9, 80.0, 77.7, 75.5, 74.9, 73.3, 72.9, 69.9, 68.4, 68.1, 62.6, 32.6, 29.48, 29.45, 29.43, 29.40, 29.27, 29.23, 26.0, 25.9 ppm; [alpha]D27+31.1 (c 1.00, CHCl3); HR-FD-MS (positive): fragment ion [M-H]+ found m/z 765.4725, C49H65O7+ requires m/z 765.4730.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14722-40-8, its application will become more common.

Reference:
Article; Kato, Eisuke; Iwano, Naoya; Yamada, Akihiko; Kawabata, Jun; Tetrahedron; vol. 67; 40; (2011); p. 7692 – 7702;,
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Application of 14722-40-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 14722-40-8 as follows.

Diol 22 (4.70 g, 19.2 mmol) was dissolved in cyclohexane (50 mL) and 48% HBr (2.4 mL, 21.2 mmol, 1.1 eq.) was added under vigorous stirring. The mixture was refluxed overnight. After cooling to r.t, saturated sodium bicarbonate solution (100 mL) was added and the phases were separated. The aqueous phase was extracted with dichloromethane (3 x 50 mL). The combined organic layers were dried over MgS04. After evaporation of the solvent the product was purified by column chromatography (silica gel, 27 chi 4 cm, cyclohexane/ethyl acetate, 4:1 ? 100% ethyl acetate) and isolated as a white solid. Yield: 3.39 g (58%). Traces of 1 ,15-dibromopentadecane were also found. 23 M.p.: 63-65 C 1H-NMR (300 MHz, CDCI3) delta [ppm]: 1 .26-1.44 (m, 23 H, 3-CH2 to 13-CH2, 1 -OH), 1 .55 (m, 2 H, 2-CH2), 1 .85 (m, 2 H, 14-CH2), 3.41 (t, 3JH,H = 6.9 Hz, 2 H, 15-CH2), 3.63 (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-13), 32.9 (t, C-14), 33.0 (t, C-2), 34.2 (t, C-15), 63.1 (t, C-1 ). Ref.: Synthesis according to C. Girlanda-Junges, F. Keyling-Bilger, G. Schmitt, B. Luu, Tetrahedron 1998, 54, 7735-7748.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14722-40-8, its application will become more common.

Reference:
Patent; WESTFAELISCHE WILHELMS-UNIVERSITAET MUENSTER; HAUFE, Guenter; LEVKAU, Bodo; SCHAEFERS, Michael; SCHILSON, Stefani Silke; KEUL, Petra; WO2013/26765; (2013); A1;,
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