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Water → (-)-1-Benzoyl-2,3-di-p-toluenesulfonyl glycerol

HRID 1074650
Notes
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Reaction equation

HRID 1074650 reaction equation
[C:1]([O:9][CH2:10][CH:11]([CH2:13][OH:14])[OH:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.[OH2:26].C(Cl)(Cl)Cl>N1C=CC=CC=1>[C:1]([O:9][CH2:10][CH:11]([CH2:13][O:14][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:22])=[O:26])[O:12][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962Water2×HCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 1379111-Monobenzoylglycerol

Product 1

HCID 12914086(-)-1-Benzoyl-2,3-di-p-toluenesulfonyl glycerolYield 72%

Reagents, catalysts & solvents 1

HCID 1049
Pyridine
Solvent

Conditions

Temperature
0 °C

Procedure

To a solution of 35.5 g (181 mmol) of (-)-1-benzoyl glycerol (G) in 250 ml of dry pyridine at 0° C. is added 83 g (433 mmol) of p-toluenesulfonyl chloride. The mixture is stirred at 0° C. for 15 minutes and then stored in a refrigerator for 144 hours. After cooling the reaction mixture to 0° C., 10 ml of water are added, the mixture is stirred for 10 minutes, and then poured into excess water. The aqueous solution is separated from the gummy product, and extracted with chloroform. The gummy residue is dissolved in chloroform and the combined chloroform solution is washed sequentially with 3 N hydrochloric acid, water, 5% sodium bicarbonate solution, and water. The chloroform solution is dried over Na2SO4 and concentrated under reduced pressure to obtain a solid which, upon recrystallization from absolute ethanol, gives 65.5 g (130 mmol, 72%) of (-)-1-benzoyl-2,3-di-p-toluenesulfonyl glycerol (see Formula (H) in Scheme 2), m.p. 105°-106° C. [α]D2° -22.7 (c, 5.92, CHCl3). 1H NMR (CDCl3) δ8-7 (m, 13H); 4.9 (m, 1H); 4.45 (d, 2H, J=6 Hz); 4.35 (d, 2H, J=5 Hz); 2.42 (s, 3H); 2.38 (s, 3H). 13C NMR (CDCl3) 165.162, 145.136, 133.108, 132.466, 131.649, 129.430, 128.671, 128.087, 127.678, 75.306, 66.899, 61.994, 21.591 ppm.

Workup

  1. waitstored in a refrigerator for 144 hours
  2. temperatureAfter cooling the reaction mixture to 0° C.
  3. stirringthe mixture is stirred for 10 minutes
  4. customThe aqueous solution is separated from the gummy product
  5. extractionextracted with chloroform
  6. dissolutionThe gummy residue is dissolved in chloroform
  7. washthe combined chloroform solution is washed sequentially with 3 N hydrochloric acid, water, 5% sodium bicarbonate solution, and water
  8. dry with materialThe chloroform solution is dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customto obtain a solid which
  11. customupon recrystallization from absolute ethanol

Sources & evidence

ORD record
ord-8ffdabc5f56d4d86a9f7b99d1f9f11ce
Source dataset
uspto-grants-1983_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04393240

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes