Ethanol → HCID 67219206, compound

HRID 2189494Notes

Reaction equation

HRID 2189494 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]([F:20])([F:19])[O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1.[CH2:21](O)[CH3:22]>>[F:6][C:7]([F:19])([F:20])[O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([O:18][CH2:21][CH3:22])=[O:17])=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 27773192-[4-(Trifluoromethoxy)phenyl]acetic acid

Product 1

HCID 67219206HCID 67219206, compoundYield 91%

Procedure

Sulfuric acid (0.484 ml, 9.08 mmol) was added dropwise to a solution of 2-(4-(trifluoromethoxy)phenyl)acetic acid (2.0 g, 9.08 mmol) in ethanol (20 ml), and heated under reflux for 5 hours. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate (100 ml), washed with saturated NaHCO3 solution and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/hexane: 0/100 to 20/80) to give ethyl 2-(4-(trifluoromethoxy)phenyl)acetate (2.06 g, yield 91%) as yellow oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiondiluted with ethyl acetate (100 ml)
  5. washwashed with saturated NaHCO3 solution and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (ethyl acetate/hexane: 0/100 to 20/80)

Sources & evidence

ORD record
ord-c60084cd80764b718d892d96daad5dc7
Source dataset
uspto-grants-2012_12
Patent number
US08324249B2

Reaction notes

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