Sodium Hydroxide → HCID 178423587, compound

HRID 476537Notes

Reaction equation

HRID 476537 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-56aa92485b1749f3a949e656fba05e81
Source dataset
uspto-grants-1989_12
Patent number
US04885022

Reaction notes

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