Hydrochloric Acid → HCID 13770772, compound

HRID 255584Notes

Reaction equation

HRID 255584 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([S:12][C:13]2[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=2[C:15]([O:17]C)=[O:16])[CH:3]=1.ClC1C=CC=C(C(OO)=[O:31])C=1.[OH-].[Na+].Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([S:12]([C:13]2[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=2[C:15]([OH:17])=[O:16])=[O:31])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 70297m-Chloroperbenzoic acidHCID 13958513HCID 13958513, compound

Product 1

HCID 13770772HCID 13770772, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethyl 4-chloro-2,2'-thiodibenzoate (6.72 g) was dissolved in methylene chloride. To the solution was added m-chloroperbenzoic acid (4 g) and the solution was stirred at room temperature for 6 hours. The reaction mixture was poured into a 10% aqueous sodium hydroxide solution and extracted with methylene chloride. The methylene chloride extract was washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered, and the filtrate was evaporated to give a product. The product was suspended into a 20% aqueous sodium hydroxide solution and heated at 60° C. for 3 hours. After cooling, the solution was acidified with 6N HCl to give a precipitate. Recrystallization from aqueous methanol gave 4-chloro-2,2'-sulfinyldibenzoic acid (compound No. 25) in an amount of 4.5 g (yield: 70%). m.p. 279-281° C.

Workup

  1. extractionextracted with methylene chloride
  2. extractionThe methylene chloride extract
  3. washwas washed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated
  7. customto give a product
  8. temperatureheated at 60° C. for 3 hours
  9. temperatureAfter cooling
  10. customto give a precipitate
  11. customRecrystallization from aqueous methanol

Sources & evidence

ORD record
ord-40be59dd3a0a4b088535ac51931c6785
Source dataset
uspto-grants-1987_10
Patent number
US04698364

Reaction notes

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