Glycerol → HCID 178527661, compound

HRID 441801Notes

Reaction equation

HRID 441801 reaction equation
[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[OH-].[Na+].[Na:9][C:10]1[CH:21]=[CH:20][C:13]([CH:14](Br)[S:15]([OH:18])(=[O:17])=[O:16])=[CH:12][CH:11]=1.O>C(O)(C)C.C(O)C.CO>[Na:9][C:10]1[CH:21]=[CH:20][C:13]([CH:14]([S:15]([OH:18])(=[O:16])=[O:17])[O:1][CH2:2][CH:3]([OH:4])[CH2:5][OH:6])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 753GlycerolHCID 962WaterHCID 14798Sodium HydroxideHCID 178527638HCID 178527638, compound

Product 1

HCID 178527661HCID 178527661, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 18681192Ethanol, mixt. with methanolSolvent

Conditions

Temperature
95 °C

Procedure

A 300-ml. beaker is charged with 18.4 parts of glycerin and 1.7 parts of sodium hydroxide. The mixture is heated to 95° C. while being stirred magnetically. To the beaker then is added 13.7 parts of 4-sodiosulfobenzyl bromide and the temperature is maintained at 95° C. for 3 hours. The viscous reaction solution then is added to 300 parts of water. The aqueous solution is concentrated to about one-tenth of its original volume and 250 parts of dimethyl sulfoxide added; isopropanol, about 200 parts, is then added resulting in a white, fluffy precipitate which is isolated by centrifugation. The solid is taken up in about 320 parts of an ethanol-methanol mixture, the volume reduced by about 25%, and isopropanol added. The product was isolated by centrifugation and dried at 60° C. under reduced pressure. The product, 3-(p-sodiosulfobenzyloxy)-1,2-propanediol, is obtained in a yield of 3 parts and has the following analysis:

Workup

  1. temperaturethe temperature is maintained at 95° C. for 3 hours
  2. concentrationThe aqueous solution is concentrated to about one-tenth of its original volume and 250 parts of dimethyl sulfoxide
  3. additionadded
  4. additionisopropanol, about 200 parts, is then added
  5. customresulting in a white, fluffy precipitate which
  6. customis isolated by centrifugation
  7. additionadded
  8. customThe product was isolated by centrifugation
  9. customdried at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-6cbe14f59a4c48f2b896489e1a355690
Source dataset
uspto-grants-1977_08
Patent number
US04042618

Reaction notes

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