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

HRID 1950827Notes

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]>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

Sodium hydroxide (5M; 10.2 mL; 51 mmol; 3 eq.) was added to a solution of methyl 2′-methyl-2-(trifluoromethyl)biphenyl-4-carboxylate (5 g; 17 mmol; 1 eq.) in EtOH (150 mL) and the reaction mixture was stirred at 60° C. for 2 hours. After concentration in vacuo, the residue was taken up in water (300 mL) and the aqueous phase was washed with ethyl acetate (2×100 mL). The pH was adjusted to 2 with conc. HCl and the solution was concentrated to ca. 150 mL. The precipitate was filtered off and dried to afford the title compound (3.33 g, 70%) as a beige solid. HPLC (Method A): Rt 4.57 min (purity 98.7%). LC/MS: 278.9 (M−H)−.

Workup

concentrationAfter concentration in vacuo
washthe aqueous phase was washed with ethyl acetate (2×100 mL)
concentrationthe solution was concentrated to ca. 150 mL
filtrationThe precipitate was filtered off
customdried

Sources & evidence

ORD record: ord-32163f21beeb4e01b6dea08111d30f8f
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404676B2

Reaction notes

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