Acetic Acid → 2-Oxo-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-propionic acid

HRID 252282Notes

Reaction equation

HRID 252282 reaction equation
C([O:3][C:4](=[CH:8][C:9]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])[CH2:12][CH2:11][CH2:10]1)[C:5]([OH:7])=[O:6])C.C(O)(=O)C.O>S(=O)(=O)(O)O>[O:3]=[C:4]([CH2:8][C:9]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:20])([F:21])[F:22])[CH2:10][CH2:11][CH2:12]1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 668669652-Ethoxy-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-acrylic acid

Product 1

HCID 596809512-Oxo-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-propionic acidYield 97.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4.6 g of 2-Ethoxy-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-acrylic acid was stirred in 100 ml of 1M sulfuric acid and 15 ml of concentrated acetic acid overnight at 100° C. Water was added, the mixture extracted with ethyl acetate, and the ethyl acetate solution was separated, dried and concentrated by evaporation in a vacuum. 4.1 g of the product was obtained as a brown oil.

Workup

  1. customat 100° C
  2. extractionthe mixture extracted with ethyl acetate
  3. customthe ethyl acetate solution was separated
  4. customdried
  5. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-9df2271e0adc4710b7f39a82af60943d
Source dataset
uspto-grants-2011_01
Patent number
US07868031B2

Reaction notes

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