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

HRID 2256973Notes

Reaction equation

HRID 2256973 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), 10 M 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-3400c30c279a4b58a99ec20ebfcd543d
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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