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Sulfuric Acid → (+)-t-Butyl-2,3-di-p-toluenesulfonyl glycerol

HRID 1074651
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1074651
C([O:9][CH2:10][CH:11]([CH2:23][O:24][S:25]([C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[O:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])(=O)C1C=CC=CC=1.[CH3:35][C:36](=[CH2:38])[CH3:37].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:36]([CH:10]([CH:11]([CH2:23][O:24][S:25]([C:28]1[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=1)(=[O:26])=[O:27])[O:12][S:13]([C:16]1[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=1)(=[O:15])=[O:14])[OH:9])([CH3:37])([CH3:35])[CH3:38]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516892Sodium BicarbonateHCID 12914086(-)-1-Benzoyl-2,3-di-p-toluenesulfonyl glycerol

Produkt 1

HCID 131713018(+)-t-Butyl-2,3-di-p-toluenesulfonyl glycerol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A solution of 13.8 g (34.5 mmol) of (-)-1,2-di-p-toluene-sulfonyl glycerol (see Formula (I) in Scheme 2) in 100 ml of dry methylenechloride is added to 100 ml of liquid isobutylene taken in a pressure bottle at -78° C. Concentrated sulfuric acid (0.2 ml) is added to the above reaction mixture, the contents are stirred, and the mixture is then allowed to warm to room temperature and stirred for 16 hours. The pressure is gradually released, and the solution is neutralized with aqueous sodium bicarbonate solution. The organic layer is separated, washed with water, and dried over Na2SO4. The solvent is removed on a rotary evaporator and the crude product is dried under reduced pressure. Recrystallization from absolute ethanol affords white crystals of (+)-t-butyl-2,3-di-p-toluenesulfonyl glycerol (see Formula (J) in Scheme 2), m.p. 70°-71° C. [α]D2 +3.44 (c, 5.9, CHCl3). 1H NMR (CDCl3)δ7.8 (m, 4H); 7.3 (m, 4H); 4.5 (m, 1H); 4.15 (d, 2H); 3.35 (d, 2H); 2.45 (s, 6H); 1.1 (s, 9H).

Aufarbeitung

  1. customtaken in a pressure bottle at -78° C
  2. stirringstirred for 16 hours
  3. customThe organic layer is separated
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customThe solvent is removed on a rotary evaporator
  7. dry with materialthe crude product is dried under reduced pressure
  8. customRecrystallization from absolute ethanol

Quellen und Nachweise

ORD-Eintrag
ord-19f4e39a2c4a4df2a9391e10741386e3
Quelldatensatz
uspto-grants-1983_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04393240

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