Hydrochloric Acid → [3-(4-Methylphenyl)sulfonyloxy-2,2-bis[(4-methylphenyl)sulfonyloxymethyl]propyl] 4-methylbenzenesulfonate

HRID 8413

Reaktionsgleichung

Reaktionsgleichung von HRID 8413
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.Cl>N1C=CC=CC=1>[S:16]([O:1][CH2:2][C:3]([CH2:8][O:9][S:16]([C:13]1[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=1)(=[O:18])=[O:17])([CH2:6][O:7][S:16]([C:13]1[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=1)(=[O:18])=[O:17])[CH2:4][O:5][S:16]([C:13]1[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=1)(=[O:18])=[O:17])([C:13]1[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=1)(=[O:18])=[O:17]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8285Pentaerythritol

Produkt 1

HCID 301538[3-(4-Methylphenyl)sulfonyloxy-2,2-bis[(4-methylphenyl)sulfonyloxymethyl]propyl] 4-methylbenzenesulfonateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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) δ 7.68 (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) δ 145.86, 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.

Aufarbeitung

  1. filtrationThe resulting white precipitate was filtered
  2. washwashed with methanol
  3. customThe solid was recrystallized from benzene

Quellen und Nachweise

ORD-Eintrag
ord-5d1a5376db894c5fa10737f03e2c124c
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087752B2

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