Potassium Hydroxide → HCID 54081071, compound

HRID 342988Notes

Reaction equation

HRID 342988 reaction equation
[Br:1][C:2]1[C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:11]([S:18][CH3:19])[CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[K+]>O>[Br:1][C:2]1[C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:11]([S:18][CH3:19])[CH:10]=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14851219HCID 14851219, compound

Product 1

HCID 54081071HCID 54081071, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-bromo-3-(2-methoxyethoxy)-4-methylsulphenylbenzoate (24.3 g) was added to a solution of potassium hydroxide (9.1 g) in water (25 ml) and industrial methylated spirits (300 ml). The resultant mixture was heated at reflux for 4 hours and then allowed to cool to room temperature overnight. The mixture was evaporated and the residue dissolved in water and washed with ether. The aqueous layer was acidified to pH 1 with 2M HCl and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness yielding 2-bromo-3-(2-methoxyethoxy)-4-methylsulphenyl benzoic acid (19.4 g) as a white solid, NMR (CDCl3) 2.2(3H,s), 3.25(3H,s), 3.6(2H,t), 3.8(2H,t), 7.0(2H,m).

Workup

  1. temperatureat reflux for 4 hours
  2. customThe mixture was evaporated
  3. dissolutionthe residue dissolved in water
  4. washwashed with ether
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried (anhydrous magnesium sulphate)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-e012fb96d36648d492872654e0fad0b6
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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