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

HRID 1074651
Notes
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Reaction equation

HRID 1074651 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-19f4e39a2c4a4df2a9391e10741386e3
Source dataset
uspto-grants-1983_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04393240

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes