Ethanol → Ethyl 4-methyl-3-(trifluoromethyl)benzoate

HRID 1946309Notes

Reaction equation

HRID 1946309 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].S(=O)(=O)(O)O.O.[CH2:21](O)[CH3:22]>C(Cl)Cl>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:21][CH3:22])=[O:7])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 27755924-Methyl-3-(trifluoromethyl)benzoic acid

Product 1

HCID 11952920Ethyl 4-methyl-3-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slight suspension of 4-methyl-3-(trifluoromethyl)benzoic acid (2.18 g, 10.7 mmol, ABCR) in ethanol (30 ml) was added concentrated sulphuric acid specific gravity 1.84 (0.5 ml, 9.38 mmol). The resulting solution was heated to reflux overnight under nitrogen. The solution was diluted with DCM (100 ml) and then water (100 ml). The phases were separated and the organic extract washed with saturated aqueous sodium hydrogen carbonate (50 ml), dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound as a mobile pale yellow oil (2.27 g); LCMS: (System 4) MH+=233, tRET=3.29 min.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux overnight under nitrogen
  3. customThe phases were separated
  4. extractionthe organic extract
  5. washwashed with saturated aqueous sodium hydrogen carbonate (50 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-33fc9be909894b4aa99015fc66305992
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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