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

HRID 219793Notes

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 g; 16.99 mmol; 1 eq.) in EtOH (150 mL) at RT was treated with sodium hydroxide (10.19 mL; 5 M; 50.97 mmol; 3 eq.). 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 HCl cc to 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), 8.26-8.23 (d, J=7.90 Hz, 1H), 7.51-7.48 (d, J=7.90 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-23b1e941530343dbbed218007f52dd70
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202865B2

Reaction notes

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