p-Toluenesulfonic acid → (+/-)-1-S-hexadecyl-2-O-ethylthioglycerol

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This compound was prepared in an analogous manner to that of (±)-1-S-hexadecyl-2-O-methylthioglycerol from 10.0 grams (0.02 mole) of (±)-1-2-hexadecyl-2-O-ethyl-3-O-tritylthioglycerol and 0.2 gram of p-toluenesulfonic acid. Silica gel chromatography (CHCl3 eluent) provided 5.8 grams (95%) of a semi-waxy solid. 1H-NMR (CDCl3): delta, 0.87(t, 3H, terminal methyl), 1.2-1.6[m, 31H, (CH2)14, CH3 --CH2 --O--], 2.58 (m, 2H, S--CH2), 2.62 (m, 2H, CH--CH2 --S), 3.40-3.50 (m, 3H, CH, CH3 --CH2 --O), 3.75(m, 2H, CH2 --OH).

Provenance & Evidence