Abstract
We report herein the syntheses of several analogues of stearic acid in which oxygen or sulfur atoms or sulfoxide groups have replaced the methylene groups at either position 9 or position 10 of the polymethylene chains. These compounds have been fully characterized by the results of proton and carbon 13 nuclear magnetic resonance, and low and high resolution mass spectral studies.
Highlights
Many derivatives of stearic acid are known in which atoms other than hydrogen are attached to carbons 9 and 10, we found no literature examples in which heteroatoms had been substituted for the carbons themselves
Packed with 3% OV-17 on Gas Chrom Q were used for the gas-liquid chromatography (GLC) analyses, and columns (20 x 0.39 cm) of Waters pBondapak CI8were used in the high performance liquid chromatography (HPLC) analyses
Octyl p-toluenesulfonate [ 'H nuclear magnetic resonance (NMR) (80 MHz, CDCl3) 6 0.87 (t, 3H, J = 7, alkyl CH3), 1.05-1.75 (m, 12H, methylene envelope), 2.44 (s, 3H, aryl CHs), 4.09 (t, 2H, J = 7, CHZSOZ), 7.33 and 7.83 (AA'BB' system, 4H, arylH4)] was prepared from I-octanol and p-toluenesulfonyl chloride according to a standard procedure (3). 9-Hydroxynonanoic acid (500 mg, 2.87 mmol) was added to a suspension of sodium hydride (60%, 0.30 g, 7.5 mmol) in dry dimethylformamide (10 ml)
Summary
This material was recrystallized from acetone to yield 8-(nony1thio)octanoic acid (5.9 g, 87%))mp 51-52OC; 'H NMR (80 MHz, CDC13) 6 0.88 (t, 3H, J = 7, CH3), 1.05-1.75 (m, 24H, methylene envelope), 2.27 (t, 2H, J = 7, CHZCOO), 2.50 (t, 4H, J = 7, CHzSCHz), 9.1 (br s, lH, COOH); 13C NMR (62.9 MHz, CDCl3) 6 14.0, 22.6, 24.6, 28.7, 28.8, 28.9*, 29.2: 29.5, 29.6, 29.7, 31.8, 32.1, 32.2, 34.0, 179.9; MS, mlz 302 (M', 22), 159 (CH3(CH~)8S',75), 83 (49), 69 (72)) 55 (100).
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