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

HRID 1868632Notes

Reaction equation

HRID 1868632 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.OS(O)(=O)=O.[CH3:20][CH2:21]O>CCOC(C)=O>[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

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

A solution of (trifluoro-p-tolyl)-acetic acid (19.85 g, 97.2 mmol) in EtOH (200 mL) was treated with H2SO4, 36N (16.4 mL, 194 mmol). The reaction was heated at reflux. After 48 hours, the reaction was cooled to 23° C., diluted with EtOAc (750 mL), washed with saturated NaHCO3 solution (2×400 mL) and brine (400 mL), dried over MgSO4, and concentrated in vacuo affording 20.98 g of ethyl 2-(4-(trifluoromethyl)phenyl)acetate.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux
  3. washwashed with saturated NaHCO3 solution (2×400 mL) and brine (400 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-45945a116edc424c849ba9c2e1c43d64
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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