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

HRID 2404297Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16]C)=[O:15])=[CH:10][C:9]=1[C:18]([F:21])([F:20])[F:19].[OH-].[Na+]>CCO.O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][C:9]=1[C:18]([F:19])([F:20])[F:21]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of methyl 2′-methyl-2-(trifluoromethyl)biphenyl-4-carboxylate (5.0 g, 17.0 mmol) in EtOH (150 mL) at RT was treated with a 5N aqueous solution of sodium hydroxide (10.2 mL, 51 mmol). The reaction mixture was stirred at 60° C. for 2 hours. The reaction mixture was concentrated to give a brown solid which was taken up in water (300 mL) and the aqueous phase was washed twice with EtOAc. The aqueous phase was acidified with a concentrated aqueous solution of HCl (pH-2), then it was concentrated until precipitation (half of the volume). The suspension was filtered affording the title compound as a beige solid. 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). LC/MS (Method A): 278.9 (M−H)−. HPLC (Method A) Rt 4.57 min (Purity: 98.7%).

Workup

concentrationThe reaction mixture was concentrated
customto give a brown solid which
washthe aqueous phase was washed twice with EtOAc
concentrationit was concentrated until precipitation (half of the volume)
filtrationThe suspension was filtered

Sources & evidence

ORD record: ord-42ad1070c95a4c94a093a463cc38ed87
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802704B2

Reaction notes

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