p-Toluenesulfonic acid → Chloralose

HRID 1196757Notes

Reaction equation

HRID 1196757 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].O=[CH:14][C:15]([Cl:18])([Cl:17])[Cl:16].CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[CH2:11]([OH:12])[C@@H:9]([OH:10])[C@H:7]1[O:8][C@@H:2]2[O:1][C@H:14]([C:15]([Cl:18])([Cl:17])[Cl:16])[O:4][C@@H:3]2[C@H:5]1[OH:6]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6407ChloralHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 7057995Chloralose

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4.5 g of glucose, 19 g of chloral, 20 ml of chloroform and 0.05 g of 4-methyl-benzene-sulphonic acid is kept at reflux temperature for 7 hours and the formed water is separated by means of a Dean-Stark apparatus. The solvent is distilled off and the residue is kept at 60° C. for 20 minutes. The sedimented material is filtrated and the pH value of the mother lye adjusted to 6.5 with sodium hydroxide. The separated precipitate is filtered.

Workup

  1. temperatureat reflux temperature for 7 hours
  2. customthe formed water is separated by means of a Dean-Stark apparatus
  3. distillationThe solvent is distilled off
  4. filtrationThe sedimented material is filtrated
  5. filtrationThe separated precipitate is filtered

Sources & evidence

ORD record
ord-b80a5b8150c544e6ac5f992ebd0d52d2
Source dataset
uspto-grants-1992_05
Patent number
US05116402

Reaction notes

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