반응 #1069775

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pentaerythritol

p-toluenesulfonyl chloride

hydrochloric acid

→

pentaerythritol tetratosylate

수율 91.0%

용매

pyridine

반응 조건

후처리

1. 1
   기타Pentaerythritol tetratosylate was prepared
2. 2
   여과The resulting white precipitate was filtered
3. 3
   세척washed with methanol
4. 4
   기타The solid was recrystallized from benzene

실험 절차

Pentaerythritol tetratosylate was prepared as follows: A mixture of pentaerythritol (27.20 grams, 199.8 mmol; obtained from Aldrich Chemical Co., Milwaukee, Wis.) and p-toluenesulfonyl chloride (171.0 grams, 897.0 mmol; obtained from Aldrich Chemical Co., Milwaukee, Wis.) in dry pyridine (300 milliliters; obtained from Anachemia) was stirred for 48 hours under nitrogen gas. This mixture was then added to 2 liters of 6 Normal hydrochloric acid. The resulting white precipitate was filtered and washed with methanol. The solid was recrystallized from benzene to afford pure pentaerythritol tetratosylate (136.5 grams, 181.3 mmol, 91 percent yield) as white crystals: mp 155-156° C.; IR (KBr) 3047, 2958, 2926, 1907, 1599, 1468, 1367, 1296, 1174, 1180, 1096, 976, 835, 666, 607, 554 cm−1; 1H NMR (400 MHz, CDCl3) δ7.68 (d, 8H, 3J=8.2 Hz) 7.36 (d, 8H, 3J=8.2 Hz), 3.82 (s, 8H), 2.47 (s, 12H); 13C NMR (100 MHz, CDCl3) δ145.86, 131.50, 130.38, 128.15, 65.74, 43.41, 21.90; MS (FAB, 3-nitrobenzyl alcohol) m/e 753; Anal. Calcd for C33H36O12S4: C, 52.64; H, 4.82: S, 17.04. Found: C, 52.98; H, 4.77; S, 17.60.

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