Sodium Hydroxide → HCID 178423587, compound

HRID 1682149Notes

Reaction equation

HRID 1682149 reaction equation
[Br:1][C:2]1[C:3]([CH3:13])=[C:4]([C:9]([CH3:12])=[CH:10][CH:11]=1)[C:5]([O:7]C)=[S:6].[OH-].[Na+]>C(O)C>[Br:1][C:2]1[C:3]([CH3:13])=[C:4]([C:9]([CH3:12])=[CH:10][CH:11]=1)[C:5]([OH:7])=[S:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53980085HCID 53980085, compound

Product 1

HCID 178423587HCID 178423587, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 100 ml of an ethanol solution containing 17.0 g of methyl 3-bromo-2-methyl-6-methylthiobenzoate, 16 g of a 50% sodium hydroxide aqueous solution was added, and the mixture was refluxed for 3 hours under heating. The reaction mixture was concentrated under reduced pressure. Then, water was added thereto, and the mixture was washed with chloroform. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with chloroform. The extract was dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 15.9 g of the desired product. Melting point: 98°-103° C.

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed for 3 hours
  3. temperatureunder heating
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionThen, water was added
  6. washthe mixture was washed with chloroform
  7. extractionextracted with chloroform
  8. dry with materialThe extract was dried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-b3dfa0c2a6164aed8c36299fe948c60d
Source dataset
uspto-grants-1992_12
Patent number
US05175299

Reaction notes

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