Sulfuric Acid → Methyl 2-(o-Methoxyphenylthio)benzoate

HRID 255926Notes

Reaction equation

HRID 255926 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].S(=O)(=O)(O)O.[C:24](=O)(O)[O-].[Na+]>CO.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([O:14][CH3:24])=[O:13]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 155738872-[(2-Methoxyphenyl)sulfanyl]benzoic acid

Product 1

HCID 13338684Methyl 2-(o-Methoxyphenylthio)benzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve 115 g of the acid of Step A in 3.5 liters of methanol and add slowly 25 ml of sulfuric acid. Stir under reflux for 72 hours. Cool the reaction mixture to room temperature and add 100 g of sodium bicarbonate in portions. Stir for an additional hour and strip to dryness. Dissolve the residue in methylene chloride and wash the solution three times with water. Dry the solution and strip to an oil which solidifies. (m.p. 82°-84° C.).

Workup

  1. temperatureunder reflux for 72 hours
  2. stirringStir for an additional hour
  3. washwash the solution three times with water
  4. customDry the solution and strip to an oil which

Sources & evidence

ORD record
ord-c9a268cd04b44c9c82fdaea328c1ec99
Source dataset
uspto-grants-1987_10
Patent number
US04699917

Reaction notes

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