Water → (Z)-3-(2-(Isopropoxycarbonyl)-3-(trifluoromethyl)phenyl)acrylic acid

HRID 2100571Notes

Reaction equation

HRID 2100571 reaction equation
C[O:2][C:3](=[O:22])/[CH:4]=[CH:5]\[C:6]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:7]=1[C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9].O.[OH-].[Li+].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C([O-])(O)=O.[Na+]>[CH:11]([O:10][C:8]([C:7]1[C:14]([C:18]([F:19])([F:21])[F:20])=[CH:15][CH:16]=[CH:17][C:6]=1/[CH:5]=[CH:4]\[C:3]([OH:22])=[O:2])=[O:9])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 10340Sodium CarbonateHCID 69052122HCID 69052122, compound

Product 1

HCID 69056742(Z)-3-(2-(Isopropoxycarbonyl)-3-(trifluoromethyl)phenyl)acrylic acidYield 92%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (Z)-isopropyl 2-(3-methoxy-3-oxoprop-1-enyl)-6-(trifluoromethyl)benzoate from Example 1, Part D (1.88 g, 5.94 mmol) in 20 mL of THF and 10 mL of water was added lithium hydroxide (157 mg, 6.53 mmol). The reaction was allowed to stir at ambient temperature for 3 h. The reaction was diluted with sat'd aq NaHCO3 and sat'd aq Na2CO3 to pH 8-9 and extracted with 1:1 hexane/ethyl acetate. The organics were discarded. The aqueous layer was acidified carefully with conc. HCl and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried (MgSO4) and concentrated in vacuo to afford 1.65 g (92%) of the title compound as a white solid. 1H NMR (CDCl3): δ 7.65 (d, 1H, J=7.7 Hz), 7.60 (d, 1H, J=7.7 Hz), 7.48 (t, 1H, J=7.7 Hz), 7.19 (d, 1H, J=12.1 Hz), 6.09 (d, 1H, J=12.1 Hz), 5.25 (septet, 1H), 1.32 (d, 6H, J=6.1 Hz). LRMS (ESI): 325.19 (M+H+Na)+.

Workup

  1. extractionextracted with 1:1 hexane/ethyl acetate
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eb6c6816ee864c0faacd6d570659d787
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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