Methanol → 3-Benzylmercapto-4-carbomethoxy benzoic acid

HRID 2072301Notes

Reaction equation

HRID 2072301 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][C:5]=1[S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CO.O.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH2:15]([S:14][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:4]=1[C:3]([O:2][CH3:1])=[O:22])[C:8]([OH:10])=[O:9])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2735133Sodium Carbonate MonohydrateHCID 53906244Benzylmercapto terephthalic acid dimethyl ester

Product 1

HCID 541082583-Benzylmercapto-4-carbomethoxy benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

50G of benzylmercapto terephthalic acid dimethyl ester is suspended in a solution of 750 ml of methanol to which is added 200 ml of a solution of 15 g of sodium carbonate monohydrate in 350 ml of water. The reaction mixture is refluxed for 30 minutes, cooled and diluted with 750 ml of water. The solid is filtered and resuspended in 375 ml of methanol and 100 ml of the above sodium carbonate solution, refluxed 30 minutes, cooled, 375 ml of water is added thereto, filtered and the damp cake resuspended in 187 ml of methanol. The remaining 50 ml of the sodium carbonate solution is then added and the reflux process repeated. The combined aqueous filtrates are acidified with 50 ml of conentrated hydrochloric acid yielding a precipitate which is filtered, washed with water and the damp cake is dissolved in ethyl acetate. The ethyl acetate solution is washed with water, dried over sodium sulfate and evaporated to yield 46 g of crude 3-benzylmercapto-4-carbomethoxy benzoic acid, which is used without further purification in part D.

Workup

  1. temperatureThe reaction mixture is refluxed for 30 minutes
  2. temperaturecooled
  3. filtrationThe solid is filtered
  4. temperature100 ml of the above sodium carbonate solution, refluxed 30 minutes
  5. temperaturecooled
  6. addition375 ml of water is added
  7. filtrationfiltered
  8. additionThe remaining 50 ml of the sodium carbonate solution is then added
  9. filtrationis filtered
  10. washwashed with water
  11. dissolutionthe damp cake is dissolved in ethyl acetate
  12. washThe ethyl acetate solution is washed with water
  13. dry with materialdried over sodium sulfate
  14. customevaporated

Sources & evidence

ORD record
ord-defb49debbbb4d62b5bde35cd77f7ff4
Source dataset
uspto-grants-1977_09
Patent number
US04051148

Reaction notes

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