Potassium Hydroxide → HCID 54327095, compound

HRID 266570Notes

Reaction equation

HRID 266570 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10]CC)=[O:9])=[C:6]([S:15][CH3:16])[C:5]=1[O:17][CH3:18]>O.C(O)C>[Br:3][C:4]1[CH:14]=[CH:13][C:7]([C:8]([OH:10])=[O:9])=[C:6]([S:15][CH3:16])[C:5]=1[O:17][CH3:18]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 54477101HCID 54477101, compound

Product 1

HCID 54327095HCID 54327095, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (2.0 g) in water was added to a solution of ethyl 4-bromo-3-methoxy-2-(methylsulphenyl)-benzoate (4.5 g) in ethanol. The resulting solution was stirred and heated at reflux for 3 hours. After cooling, the mixture was evaporated to dryness and the residue was dissolved in water and washed with ethyl acetate. The aqueous solution was acidified to pH 1 and extracted with ethyl acetate, dried (anhydrous MgSO4) and filtered. The filtrate was evaporated to dryness to give 4-bromo-3-methoxy-2-(methylsulphenyl)benzoic acid as a white solid, NMR (CDCl3) 2.5(s,3H), 3.9(s,3H), 7.4(s,2H), 10.9(bs, 1H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. customthe mixture was evaporated to dryness
  5. dissolutionthe residue was dissolved in water
  6. washwashed with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. dry with materialdried (anhydrous MgSO4)
  9. filtrationfiltered
  10. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-a4821d5211594b78ae1bd9e2753a76c6
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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