4-Hydroxybenzenesulfonic acid → HCID 178527625, compound

HRID 441798Notes

Reaction equation

HRID 441798 reaction equation
[OH-:1].[K+:2].[CH:3]1[C:8](O)=[CH:7][CH:6]=[C:5]([S:10]([OH:13])(=[O:12])=[O:11])[CH:4]=1.Cl[CH2:15][CH:16]([OH:19])[CH2:17][OH:18]>O>[K:2][C:3]1[CH:8]=[CH:7][C:6]([O:1][CH2:15][CH:16]([OH:19])[CH2:17][OH:18])=[C:5]([S:10]([OH:13])(=[O:12])=[O:11])[CH:4]=1

Participants

5

Reactant 3

HCID 47654-Hydroxybenzenesulfonic acidHCID 72903-Chloro-1,2-propanediolHCID 14797Potassium Hydroxide2×

Product 1

HCID 178527625HCID 178527625, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using the same apparatus as described in Example I, the flask is charged with 4000 parts of water and 1318 parts of potassium hydroxide (85%). The mixture is stirred until a solution is obtained. To the flask then is added 2670 parts of a 65% aqueous solution of p-phenolsulfonic acid, followed by 1100 parts of 3-chloro-1,2-propanediol. The resultant solution is refluxed for about 24 hours. The pH is adjusted to 8 by adding 25% aqueous potassium hydroxide solution. The solution is concentrated by heating under reduced pressure and then is cooled to 20°-25° C. by placing the flask in a cold water-bath. Solid precipitates. The solid is isolated by suction filtration and washed three times with 4:1 ethanol-water. The dried product, 3-(4-potassiosulfophenoxy)-1,2-propanediol, is obtained in a yield of 2030 parts and with a purity of 97%, based upon adjacent hydroxyl group analysis; chloride content is 0.03%. Thermal gravimetric analysis of the product shows that there is no weight loss at 300° C.

Workup

  1. customis obtained
  2. concentrationThe solution is concentrated
  3. temperatureby heating under reduced pressure
  4. temperatureis cooled to 20°-25° C.
  5. customSolid precipitates
  6. customThe solid is isolated by suction filtration
  7. washwashed three times with 4:1 ethanol-water

Sources & evidence

ORD record
ord-024dc2a4bb2e4fe8ab9c8e978dfb9209
Source dataset
uspto-grants-1977_08
Patent number
US04042618

Reaction notes

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