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ChemicalBook CAS DataBase List ISOSTEARIC ACID

ISOSTEARIC ACID synthesis

6synthesis methods
-

Yield:2724-58-5 82%

Reaction Conditions:

with potassium permanganate;tetrabutylammomium bromide;acetic acid in dichloromethane;water for 24 h;Reflux;

Steps:

16-Methylheptadecanoic acid (7; iso-C18 acid)
The alcohol 25 (8.50 g, 31.4 mmol) was subjected to the same conditions as described for compound 12 (in the preparation of 2), affording 7 as a lustrous white solid with a strong odor (7.39 g, 82%); mp 68-69 °C (lit. [3] mp 69.5 °C); 1H NMR (500 MHz, CDCl3) δ 0.87 (6H, d, J = 6.6 Hz), 1.12-1.19 (2H, m), 1.24-1.39 (22H, m), 1.52 (1H, t of sept, J = 6.6, 6.6 Hz), 1.64 (2H, tt, J = 7.5, 7.5 Hz), 2.35 (2H, t, J = 7.5 Hz); 13C NMR (125 MHz, CDCl3) δ 22.8, 24.8, 27.6, 28.1, 29.2, 29.4, 29.6, 29.75, 29.79, 29.82, 29.84, 29.85, 29.9, 30.1, 34.2, 39.2, 179.7; IR 1698, 2851, 2917 cm-1; HRMS (ESI-) calcd for C18H35O2 [M - H]- m/z 283.2643, found 283.2636.

References:

Richardson, Mark B.;Williams, Spencer J. [Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1807 - 1812] Location in patent:supporting information

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