Water → 2'-Methyl-2-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acid

HRID 1630975Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A 5N aqueous solution of NaOH (10.2 mL, 51.0 mmol) was added into a solution of methyl 2′-methyl-2-(trifluoromethyl)biphenyl-4-carboxylate (5.00 g, 17.0 mmol) in EtOH (150 mL). The resulting mixture was stirred at 60° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure to give a brown solid. The residue was taken up with water (300 mL) and washed twice with EtOAc. The aqueous layer was acidified with a concentrated aqueous solution of HCl until pH=2, and then concentrated until precipitation (half of the volume). The precipitate was filtered off affording the title compound as a beige solid (3.33 g, 70%). 1H NMR (DMSO-d6, 300 MHz) δ 13.55 (br s, 1H), 8.31 (s, 1H), 8.25 (d, J=7.9 Hz, 1H), 7.50 (d, J=7.9 Hz, 1H), 7.37-7.12 (m, 4H), 1.99 (s, 3H). HPLC (Method A), Rt 4.6 min (Purity: 98.7%). UPLC/MS, M−(ESI): 279.2.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customto give a brown solid
washwashed twice with EtOAc
concentrationconcentrated until precipitation (half of the volume)
filtrationThe precipitate was filtered off

Sources & evidence

ORD record: ord-bb6a23b3d46f4f6fa827d937e4d186de
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791142B2

Reaction notes

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