Lithium Hydroxide → 3-(2-Propyl-4-trifluoromethyl-phenyl)-acrylic acid

HRID 1042470Notes

Reaction equation

HRID 1042470 reaction equation
C[O:2][C:3](=[O:19])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=1[CH2:16][CH2:17][CH3:18].[Li+].[OH-]>C1COCC1.O>[CH2:16]([C:7]1[CH:8]=[C:9]([C:12]([F:13])([F:15])[F:14])[CH:10]=[CH:11][C:6]=1[CH:5]=[CH:4][C:3]([OH:19])=[O:2])[CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 668554943-(2-Propyl-4-trifluoromethyl-phenyl)-acrylic acid methyl ester

Product 1

HCID 668558853-(2-Propyl-4-trifluoromethyl-phenyl)-acrylic acidYield 74.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-(2-propyl-4-trifluoromethyl-phenyl)-acrylic acid methyl ester (220 mg, 0.81 mmol) in THF (3 mL) was added a solution of 1N-LiOH (6 ml), and the mixture was stirred for 3 hours at room temperature. The reaction mixture was diluted with H2O, which was washed three times with EtOAc, acidified with 1N HCl to pH 1-2. The resulting solution was extracted three times with methylene chloride and then dried over anhydrous MgSO4 and concentrated in vacuo to give the title compound (155 mg, 74%).

Workup

  1. washwas washed three times with EtOAc
  2. extractionThe resulting solution was extracted three times with methylene chloride
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0412593cba6d4241acb54ea9dce995d6
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

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