p-Toluenesulfonic acid → beta-Chloralose

HRID 1196758Notes

Reaction equation

HRID 1196758 reaction equation
[CH3:1]C1C=CC(S(O)(=O)=O)=CC=1.[O:12]=[CH:13][C@@H:14]([C@H:16]([C@@H:18]([C@@H:20]([CH2:22][OH:23])[OH:21])[OH:19])[OH:17])[OH:15].[CH:24]([Cl:27])([Cl:26])[Cl:25]>>[CH2:22]([OH:23])[C@@H:20]([OH:21])[C@H:18]1[O:19][C@@H:13]2[O:12][C@@H:1]([C:24]([Cl:27])([Cl:26])[Cl:25])[O:15][C@@H:14]2[C@H:16]1[OH:17]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6212ChloroformHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 5284343beta-Chloralose

Procedure

Under stirring 0.05 g of 4-methyl-benzene sulphonic acid and 20 ml of chloroform are added to a mixture of 4.5 g of glucose and 19 g of choral. The mixture is heated to reflux temperature and the formed water is separated by means of a Dean-Stark apparatus. The solvent is distilled off, then the mixture is kept at a temperature of 60° C. for 20 minutes. The separated material is filtered off.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux temperature
  3. customthe formed water is separated by means of a Dean-Stark apparatus
  4. distillationThe solvent is distilled off
  5. filtrationThe separated material is filtered off

Sources & evidence

ORD record
ord-d53c1fbb33c249efbc3cc08fedce34e7
Source dataset
uspto-grants-1992_05
Patent number
US05116402

Reaction notes

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