4-Toluenesulfonyl chloride → 1,6-Di-O-(p-toluenesulphonyl)-2,5-anhydro-D-mannitol

HRID 459422

Reaction equation

HRID 459422 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([OH:22])[C@H:13]1[O:19][C@H:18]([CH2:20][OH:21])[C@@H:16]([OH:17])[C@@H:14]1[OH:15]>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:21][CH2:20][C@H:18]2[O:19][C@H:13]([CH2:12][O:22][S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=3)(=[O:9])=[O:8])[C@@H:14]([OH:15])[C@@H:16]2[OH:17])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 735442,5-anhydro-D-mannitol

Product 1

HCID 140769161,6-Di-O-(p-toluenesulphonyl)-2,5-anhydro-D-mannitol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5.33 g (27.945 mmol) of p-toluenesulphonyl chloride were added at 0° C. to a solution of 2.16 g (13.15 mmol) of 2,5-anhydro-D-mannitol in 88 ml of pyridine. The mixture was heated to room temperature and stirred for a further 24 hours. The reaction was hydrolysed using ice-water and extracted using CH2Cl2, and the combined organic phases were washed with 3N HCl and NaCl. After drying over MgSO4, the solvent was subsequently removed under reduced pressure. The crude product was purified by means of column chromatography (hexane/ethyl acetate 1:2). Yield: 3.00 g (48% of theory).

Workup

  1. extractionextracted
  2. washthe combined organic phases were washed with 3N HCl and NaCl
  3. dry with materialAfter drying over MgSO4
  4. customthe solvent was subsequently removed under reduced pressure
  5. customThe crude product was purified by means of column chromatography (hexane/ethyl acetate 1:2)

Sources & evidence

ORD record
ord-0dd59ae4d97a4658b66d6ba2925c3377
Source dataset
uspto-grants-2007_03
Patent number
US07193092B2

Linked notes

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