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

HRID 982593

반응식

HRID 982593 반응식
[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]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8285Pentaerythritol

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

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.

후처리

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

출처 및 근거

ORD 기록
ord-83e2b0f0d417451faeeb62a62da99aee
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06860928B2

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