Ethanol → 2-(1-Methylpropylsulphenyl)-4-trifluoromethylbenzoic acid

HRID 2393031Notes

Reaction equation

HRID 2393031 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]>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

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 2-(1-methylpropylsulphenyl)-4-trifluoromethylbenzonitrile (8.6 g) in ethanol was added to a solution of sodium hydroxide (47.3 g) in water and the resultant mixture was heated at reflux for 24 hours. It was poured into water and acidified to pH 1. The mixture was extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 2-(1-methylpropylsulphenyl)-4-trifluoromethylbenzoic acid (8.1 g) as a white solid, m.p. 99.8°-101° C.

Workup

  1. temperatureat reflux for 24 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-9831645fb27d4d10a013e8d99a2c49ff
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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