Thioglycolic Acid → Sodium 2,5-dichlorophenylthioglycolate

HRID 248596

Reaction equation

HRID 248596 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[Cl:9].[C:10]([OH:14])(=[O:13])[CH2:11][SH:12].[OH-].[Na+:16]>CS(C)=O>[Cl:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[CH:11]([SH:12])[C:10]([O-:14])=[O:13].[Na+:16]

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 14798Sodium HydroxideHCID 150332-Bromo-1,4-dichlorobenzene

Product 1

HCID 86746839Sodium 2,5-dichlorophenylthioglycolate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a 300 ml four-necked flask equipped with a stirrer, a thermometer and a condenser were charged 24.9 g (0.110 mol) of 1-bromo-2,5-dichlorobenzene, 13.19 g (0.143 mol) of thioglycolic acid, 12.06 g (0.286 mol) of 95% sodium hydroxide and 100 g of dimethylsulfoxide, followed by stirring at 120° C. for 4 hours. Then, after distilling off the dimethylsulfoxide under reduced pressure, 100 g of water was added to the residue. After dissolving the residue therein at 100° C., the solution was cooled for crystallization and filtered to yield sodium 2,5-dichlorophenylthioglycolate, which was then dissolved in 100 g of water with heating and acidized with concentrated hydrochloric acid, filtered and dried to yield 19.6 g of a light yellowish white powder of 2,5-dichlorophenylthioglycolic acid. The yield based on 1-bromo-2,5-dichlorobenzene was 75.1%.

Workup

  1. customTo a 300 ml four-necked flask equipped with a stirrer
  2. distillationThen, after distilling off the dimethylsulfoxide under reduced pressure, 100 g of water
  3. additionwas added to the residue
  4. dissolutionAfter dissolving the residue
  5. temperatureat 100° C., the solution was cooled for crystallization
  6. filtrationfiltered

Sources & evidence

ORD record
ord-b1a8a31e9ef0488788efa04fab918a4b
Source dataset
uspto-grants-1993_05
Patent number
US05210291

Linked notes

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