Ethanol → 3-(3-Trifluoromethylphenyl)-2-(4-trifluoromethylphenyl)-propionic acid

HRID 2222754Notes

Reaction equation

[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5](/[CH:9]=[C:10](/[C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)\[C:11]([OH:13])=[O:12])[CH:6]=[CH:7][CH:8]=1.C(O)C.C([O-])=O.[NH4+].C(OCC)(=O)C>[Pd].C(O)(=O)C>[F:1][C:2]([F:24])([F:25])[C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:16][CH:15]=2)[C:11]([OH:13])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A three neck, one liter round bottom flask equipped with condenser, thermometer, nitrogen line and magnetic stirrer was charged with Z-3-(3-trifluoromethylphenyl)-2-(4-trifluoromethylphenyl)-acrylic acid (103, 2.28 g, 6.3 mmol), ethanol (104 mL), palladium black (101.1 mg) and ammonium formate (1.608 g, 25.5 mmol). The reaction mixture was heated to 80° C. for 4 hours. An aliquot was taken and TLC (solvent system was 20% ethyl acetate in hexanes with an acetic acid spike) showed absence of starting material. The solution was cooled to room temperature and vacuum filtered using a glass frit funnel. The solution was concentrated by rotary evaporation and high vaccum, yielding 3-(3-trifluoromethylphenyl)-2-(4-trifluoromethylphenyl)-propionic acid (2.83 g) 105.

Workup

customA three neck, one liter round bottom flask equipped with condenser
temperatureThe solution was cooled to room temperature
filtrationvacuum filtered
concentrationThe solution was concentrated by rotary evaporation and high vaccum

Sources & evidence

ORD record: ord-d626d3f3e21f48b6bedb8173e6626d07
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371888B2

Reaction notes

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