Ethanol → 2-Ethoxy-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-acrylic acid

HRID 252281Notes

Reaction equation

HRID 252281 reaction equation
C([O:3][C:4](=[O:24])[C:5]([O:21][CH2:22][CH3:23])=[CH:6][C:7]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])[CH2:10][CH2:9][CH2:8]1)C.[OH-].[Na+].C(O)C>O>[CH2:22]([O:21][C:5](=[CH:6][C:7]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:18])([F:19])[F:20])[CH2:10][CH2:9][CH2:8]1)[C:4]([OH:24])=[O:3])[CH3:23]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 668666852-Ethoxy-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-acrylic acid ethyl ester

Product 1

HCID 668669652-Ethoxy-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-acrylic acidYield 101.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.6 g of 2-Ethoxy-3-[1-(2-trifluoromethyl-phenyl)-cyclobutyl]-acrylic acid ethyl ester, 4.3 g of sodium hydroxide, 100 ml ethanol and 50 ml water (ethanol-water 2:1) were mixed and stirred for 2 hours at room temperature. Solvent was evaporated in vacuum, residue was distributed between water and ethyl acetate, and water solution was acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate extracts were washed with saturated aqueous sodium chloride solution, dried and concentrated by evaporation in a vacuum. 4.3 g of product was obtained and used for the next reaction without further purification.

Workup

  1. customSolvent was evaporated in vacuum, residue
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate extracts were washed with saturated aqueous sodium chloride solution
  4. customdried
  5. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-f2996b701f034843864ef37ab86bc024
Source dataset
uspto-grants-2011_01
Patent number
US07868031B2

Reaction notes

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