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

HRID 1042453Notes

Reaction equation

HRID 1042453 reaction equation
C[O:2][C:3](=[O:20])[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[O:16][CH2:17][CH2:18][CH3:19].[Li+].[OH-]>C1COCC1.CO>[CH2:17]([O: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:20])=[O:2])[CH2:18][CH3:19]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66856006HCID 66856006, compound

Product 1

HCID 668569423-(2-Propoxy-4-trifluoromethyl-phenyl)-acrylic acidYield 72.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Propoxy-4-trifluoromethyl-phenyl)-acrylic acid methyl ester (198 mg) was reacted with 1N LiOH (5 ml) in THF (10 ml) and CH3OH (5 ml) for 1 hr. The reaction mixture was concentrated in vacuo. Water (30 ml) was added to the resulting residue, which was neutralized with 1N HCl solution. The mixture was extracted with ethyl acetate (30 ml×3). The combined organic layer was dried over MgSO4. The filterate was concentrated in vacuo to yield title compound (136 mg, 72%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionWater (30 ml) was added to the resulting residue, which
  3. extractionThe mixture was extracted with ethyl acetate (30 ml×3)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. concentrationThe filterate was concentrated in vacuo

Sources & evidence

ORD record
ord-fcbc6f2df0d544258ab5ae90d9565259
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

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