Potassium Hydroxide → HCID 54301627, compound

HRID 2256921Notes

Reaction equation

HRID 2256921 reaction equation
[OH-].[K+].[Br:3][C:4]1[C:14]([O:15][CH3:16])=[C:13]([S:17][CH2:18][CH3:19])[CH:12]=[CH:11][C:5]=1[C:6]([O:8]CC)=[O:7]>O.C(O)C>[Br:3][C:4]1[C:14]([O:15][CH3:16])=[C:13]([S:17][CH2:18][CH3:19])[CH:12]=[CH:11][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 53955163HCID 53955163, compound

Product 1

HCID 54301627HCID 54301627, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (1.46 g) in water was added to a mixture of ethyl 2-bromo-4-ethylsulphenyl-3-methoxybenzoate (3.98 g) in ethanol with stirring. The mixture was stirred and heated at reflux for 4 hours. It was cooled and evaporated then water was added and the mixture was washed with ethyl acetate then acidified to pH1. It was extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 2-bromo-4-ethylsulphenyl-3-methoxybenzoic acid as an off-white solid NMR (CDCl3) 1.5(t,3H) 3.05(q,2H) 3.9(s,3H) 7.15(d, 1H) 7.6(d, 1H).

Workup

  1. stirringThe mixture was stirred
  2. temperatureheated
  3. temperatureat reflux for 4 hours
  4. temperatureIt was cooled
  5. customevaporated
  6. additionwater was added
  7. washthe mixture was washed with ethyl acetate
  8. extractionIt was extracted with ethyl acetate
  9. washwashed with water
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-453b3d694e3d443987a63971381af8ab
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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