Chloroacetic Acid → HCID 178526159, compound

HRID 1389460Notes

Reaction equation

HRID 1389460 reaction equation
[Cl:1][CH2:2][C:3](O)=O.[C:6](=O)(O)[O-].[Na+].Cl[C:12]1[CH:17]=C[C:15]([SH:18])=[CH:14][CH:13]=1.[OH-:19].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:6][C:13]([CH2:14][C:15]([OH:19])=[S:18])=[CH:12][CH:17]=1

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 7815p-ChlorothiophenolHCID 14798Sodium HydroxideHCID 516892Sodium Bicarbonate

Product 1

HCID 178526159HCID 178526159, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

72.0 g. (0.76 mole) of α-chloroacetic acid, 40.0 g. of sodium bicarbonate, and 2 l. of water were placed in a 4 l. beaker and 110 g. (0.76 mole) of p-chlorobenzenethiol and 30 g. of sodium hydroxide in 200 ml. of water were added. After 0.5 to 2 hrs. on a steam bath the mixture was cooled, filtered, and the filtrate treated with 41 ml. of sulfuric acid (previously diluted to 100 ml. with water). The product was collected on a Buchner funnel and purified by dissolving in dilute aqueous sodium hydroxide, then treated with activated charcoal, filtered, and acidified. There was obtained in this manner, 78.5% yield of the final product, m.p. 105.5°-106° C.

Workup

  1. temperatureon a steam bath the mixture was cooled
  2. filtrationfiltered
  3. additionthe filtrate treated with 41 ml
  4. additionof sulfuric acid (previously diluted to 100 ml
  5. customThe product was collected on a Buchner funnel
  6. custompurified
  7. dissolutionby dissolving in dilute aqueous sodium hydroxide
  8. additiontreated with activated charcoal
  9. filtrationfiltered

Sources & evidence

ORD record
ord-d0c96f5767354f0e99b7ed666ff716b1
Source dataset
uspto-grants-1981_01
Patent number
US04244963

Reaction notes

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