Lithium Hydroxide → HCID 178506741, compound

HRID 441799Notes

Reaction equation

HRID 441799 reaction equation
[OH2:1].[OH-].[Li+:3].[CH:4]1[C:9](O)=[CH:8][CH:7]=[C:6]([S:11]([OH:14])(=[O:13])=[O:12])[CH:5]=1.Cl[CH2:16][CH:17]([OH:20])[CH2:18][OH:19].[OH-].[Li+]>O>[Li:3][C:4]1[CH:9]=[CH:8][C:7]([O:1][CH2:16][CH:17]([OH:20])[CH2:18][OH:19])=[C:6]([S:11]([OH:14])(=[O:13])=[O:12])[CH:5]=1

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 47654-Hydroxybenzenesulfonic acidHCID 72903-Chloro-1,2-propanediolHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 178506741HCID 178506741, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
104 °C

Procedure

Using the same apparatus as described in Example I, the flask is charged with 4000 parts of water and 840 parts of lithium hydroxide, monohydrate. 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 heated at reflux (about 104° C.) for about 24 hours. The pH is adjusted to 8 by adding 25% aqueous lithium hydroxide solution. The solution is concentrated by heating under reduced pressure and then is cooled at 20°-25°C. C by placing the flask in a cold water-bath. Solid precipitates. The solid is isolated by suction filtration and washed three times with 1000 parts of isopropanol. The solid then is reslurried in 9:1 isopropanol-water, filtered, and washed several times with 9:1 isopropanol-water. The isolated product is reslurried, filtered, and washed a second time. The dried product, 3-(4-lithiosulfophenoxy)-1,2-propanediol, is obtained in a yield of 980 parts and with a purity of 99%, based upon adjacent hydroxyl group analysis; the product contains 0.05% chloride. Elemental analysis of the product gives the following results:

Workup

  1. customis obtained
  2. concentrationThe solution is concentrated
  3. temperatureby heating under reduced pressure
  4. temperatureis cooled at 20°-25°C
  5. customSolid precipitates
  6. customThe solid is isolated by suction filtration
  7. washwashed three times with 1000 parts of isopropanol
  8. filtrationfiltered
  9. washwashed several times with 9:1 isopropanol-water
  10. filtrationfiltered
  11. washwashed a second time

Sources & evidence

ORD record
ord-070660f4bcd34b889b6c89f1f775f09d
Source dataset
uspto-grants-1977_08
Patent number
US04042618

Reaction notes

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