Ethanol → HCID 54141100, compound

HRID 1288766Notes

Reaction equation

HRID 1288766 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[C:6]([S:14][CH3:15])[C:5]=1[C:16]([CH3:18])=[CH2:17].C(O)C>O>[Cl:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[C:6]([S:14][CH3:15])[C:5]=1[C:16]([CH3:18])=[CH2:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 53939773HCID 53939773, compound

Product 1

HCID 54141100HCID 54141100, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (7.0 g) in water was added to methyl 4-chloro-3-isopropenyl-2-(methylsulphenyl)benzoate (7.3 g) and the resulting mixture was heated at reflux for 2 hours. Ethanol was added and the mixture was heated at reflux for 1 hour. The ethanol was removed by evaporation and the aqueous residue was acidified to pH 1. It was extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 4-chloro-3-isopropenyl-2-(methylsulphenyl)benzoic acid (6.15 g) NMR (CDCl3) 2.05 (s,3H), 2.4 (s,3H), 4.85 (s,1H), 5.35 (s,1H), 7.45 (d,1H), 7.85 (d,1H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 1 hour
  5. customThe ethanol was removed by evaporation
  6. extractionIt was extracted with ethyl acetate
  7. washwashed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-6080012926d14c00bcf4682686a878fe
Source dataset
uspto-grants-1998_05
Patent number
US05747424

Reaction notes

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