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

HRID 982593

Reaction equation

HRID 982593 reaction equation
[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]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8285Pentaerythritol

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-83e2b0f0d417451faeeb62a62da99aee
Source dataset
uspto-grants-2005_03
Patent number
US06860928B2

Linked notes

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