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

HRID 1038665

Reaction equation

HRID 1038665 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.[CH2:20](O)[CH3:21]>>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:20][CH3:21])=[O:7])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

4

Reactant 3

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

Product 1

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

Procedure

A solution of commercially available 4-methyl-3-trifluoromethylbenzoic acid (24.5 g, 120 mmol) and conc. sulfuric acid (6.5 ml) in dry ethanol (245 ml) is refluxed for 23 h. After reaching room temperature the solvent is evaporated and the residue is neutralized by addition of saturated aqueous NaHCO3 solution. The mixture is extracted with ethyl acetate (3×40 ml). The organic extracts are combined, dried over Na2SO4 and evaporated to dryness to afford a pale yellow oil: HPLC: tR=7.15 min (purity: >96%, gradient A), ESI-MS: 233.3 [MH]+.

Workup

  1. customAfter reaching room temperature
  2. customis evaporated
  3. additionthe residue is neutralized by addition of saturated aqueous NaHCO3 solution
  4. extractionThe mixture is extracted with ethyl acetate (3×40 ml)
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customto afford a pale yellow oil

Sources & evidence

ORD record
ord-12b25178549c4aba98b40378a1cdd289
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Linked notes

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