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

HRID 2078040Notes

Reaction equation

HRID 2078040 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-2e659d3826ea4f5182ad82d818af361d
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

Loading…