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

HRID 977905Notes

Reaction equation

HRID 977905 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>[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

5

Reactant 3

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

Product 1

HCID 13338684Methyl 2-(o-Methoxyphenylthio)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 115 gm of the acid of Step A in 3.5 1. of methanol and add slowly 25 cc of sulfuric acid. Stir under reflux for 72 hours. Cool the reaction mixture to room temperature.and add 100 gm of sodium bicarbonate in portions. Stir for an additional hour, filter and strip the filtrate 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. filtrationfilter
  4. dissolutionDissolve the residue in methylene chloride
  5. washwash the solution three times with water
  6. customDry the solution and strip to an oil which

Sources & evidence

ORD record
ord-a293ede04b8d45c789e64f50873626cf
Source dataset
uspto-grants-1987_05
Patent number
US04663307

Reaction notes

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