Hydrochloric Acid → 2-(1-Methylpropylsulphenyl)-4-trifluoromethylbenzoic acid

HRID 1288775Notes

Reaction equation

HRID 1288775 reaction equation
[CH3:1][CH:2]([S:5][C:6]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10]C=1C#N)[CH2:3][CH3:4].[OH-:18].[Na+].[CH2:20]([OH:22])[CH3:21].Cl>O>[CH3:1][CH:2]([S:5][C:6]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:21]=1[C:20]([OH:18])=[O:22])[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 543393872-(1-Methylpropylsulphenyl)-4-trifluoromethylbenzonitrile

Product 1

HCID 538113432-(1-Methylpropylsulphenyl)-4-trifluoromethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(1-Methylpropylsulphenyl)-4-trifluoromethylbenzonitrile (8.6 g), 10M sodium hydroxide (120 ml) and ethanol were combined and heated at reflux for 24 hours. The cooled mixture was poured into water and acidified to pH 1 with concentrated hydrochloric acid. The mixture was extracted with ethyl acetate. The organic phase was washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness yielding 2-(1-methylpropylsulphenyl)-4-trifluoromethylbenzoic acid (8.1 g) as a white solid, m.p. 99.8°-101° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried (anhydrous magnesium sulphate)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-b331539e5be44690b4bd024ea87d9468
Source dataset
uspto-grants-1998_05
Patent number
US05747424

Reaction notes

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