Stannous Chloride → 3-(5-Carboxy-2-methoxy-phenyldisulfanyl)-4-methoxy-benzoic acid

HRID 2094705Notes

Reaction equation

HRID 2094705 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8]([OH:10])=[O:9])(=O)=O.[Sn](Cl)Cl>C(O)(=O)C.Cl>[C:8]([C:7]1[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:5]([S:2][S:2][C:5]2[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=2[O:14][CH3:15])[C:8]([OH:10])=[O:9])[CH:6]=1)([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 38548883-(Chlorosulfonyl)-4-methoxybenzoic acid

Product 1

HCID 124257513-(5-Carboxy-2-methoxy-phenyldisulfanyl)-4-methoxy-benzoic acidYield 99.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
40 °C

Procedure

45 g (179.5 mmol) of 3-chlorosulfonyl-4-methoxy-benzoic acid were suspended in 200 ml of acetic acid and warmed to 40° C. Then a solution of 85.1 g (448.8 mmol) tin(II) chloride in 100 ml of hydrochloric acid was added within 15 min and the mixture was stirred for 2 h under reflux. The hot solution was added dropwise to 2000 ml of ice/water. The formed precipitate was collected by suction, washed with water and dried. 32.8 g of the title compound were obtained.

Workup

  1. temperatureunder reflux
  2. customThe formed precipitate was collected by suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-af4337e4af604713920bc4828f0b60f4
Source dataset
uspto-grants-2013_05
Patent number
US08445530B2

Reaction notes

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