Ethanol → Ethyl (4-(trifluoromethyl)phenyl)acetate

HRID 1667290Notes

Reaction equation

HRID 1667290 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH2:20](O)[CH3:21]>>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH2:20][CH3:21])=[O:11])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acid

Product 1

HCID 14134124Ethyl (4-(trifluoromethyl)phenyl)acetate

Procedure

2-(4-(Trifluoromethyl)phenyl)acetic acid (5.0 g, 24.49 mmol) was dissolved in ethanol (100 mL). Concentrated sulfuric acid (1 mL) was added, and the mixture was refluxed overnight. After cooling to room temperature, the reaction mixture was concentrated and diluted with diethyl ether. The organic solvent solution was then extracted with water, saturated aqueous sodium bicarbonate solution, and brine. The organic layer was then dried with magnesium sulfate, filtered, and concentrated to obtain the title compound. MS (DCI+) m/z 250 (M+NH4)+.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. concentrationthe reaction mixture was concentrated
  3. additiondiluted with diethyl ether
  4. extractionThe organic solvent solution was then extracted with water, saturated aqueous sodium bicarbonate solution, and brine
  5. dry with materialThe organic layer was then dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d8a5426e37f94f3a94ce5707c4fc0e4f
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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