Sodium Hydroxide → 2-Chloro-3-ethylthiomethyl-4-methanesulfonylbenzoic acid

HRID 1682146Notes

Reaction equation

HRID 1682146 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:13]([CH2:14][S:15][CH2:16][CH3:17])=[C:12]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7]>CO>[Cl:3][C:4]1[C:13]([CH2:14][S:15][CH2:16][CH3:17])=[C:12]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15132839Methyl 2-chloro-3-ethylthiomethyl-4-methanesulfonylbenzoate

Product 1

HCID 151328402-Chloro-3-ethylthiomethyl-4-methanesulfonylbenzoic acidYield 93.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution mixture comprising 50 ml of a 10% sodium hydroxide aqueous solution and 150 ml of methanol, 3.9 g of methyl 2-chloro-3-ethylthiomethyl-4-methanesulfonylbenzoate was added, and the mixture was stirred at room temperature for 30 minutes. Methanol was distilled off under reduced pressure, and a dilute hydrochloric acid was added to the residue for acid precipitation. The mixture was extracted with ethyl acetate, and the extract was dried. Then, the solvent was distilled off to obtain 3.5 g of the desired product. Melting point: 172°-174° C.

Workup

  1. additionwas added
  2. distillationMethanol was distilled off under reduced pressure
  3. additiona dilute hydrochloric acid was added to the residue for acid precipitation
  4. extractionThe mixture was extracted with ethyl acetate
  5. customthe extract was dried
  6. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-39f22ede9f8a4b6e9142d4fa1675d64d
Source dataset
uspto-grants-1992_12
Patent number
US05175299

Reaction notes

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