tert-Butanol → 4-(Trifluoromethyl)-[1,1'-biphenyl]-2-carboxylic acid

HRID 483286Notes

Reaction equation

[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10](C=O)=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.[Mn]([O-])(=O)(=O)=O.[K+].[OH-:25].[Na+].[C:27]([OH:31])(C)(C)C>O>[F:18][C:2]([F:1])([F:17])[C:3]1[CH:4]=[C:5]([C:27]([OH:31])=[O:25])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4'-Trifluoromethyl-2-biphenylcarbaldehyde (1.08 g, 4.32 mmol) in tert-butanol (15 mL) at 80° C. was added a solution of potassium permanganate (0.89 g, 5.62 mmol) in water (25 mL). After stirring at 80° C. for two hours, the mixture was cooled, a solution of 3N sodium hydroxide was added (2 mL) and the manganese dioxide was filtered off. The filtrate was diluted with water (15 mL) and acidified with 6N hydrochloric acid to precipitate the title compound (1.05 g, 91.2%). Dissolution in 0.3N sodium hydroxide (15 mL), followed by charcoal treatment, filtrating, and precipitation with 6N hydrochloric acid gave the purified 4-Trifluoromethyl-2-biphenylcarboxylic acid compound (0.85 g, 85%). 'H NMR (CDCl3): 7.5 (m, 7, ArH), 8.0 (m, 1,3-H), 9.5 (broad s, 1, CO2H).

Workup

temperaturethe mixture was cooled
filtrationthe manganese dioxide was filtered off
additionThe filtrate was diluted with water (15 mL)
customto precipitate the title compound (1.05 g, 91.2%)
dissolutionDissolution in 0.3N sodium hydroxide (15 mL)
filtrationfiltrating
customprecipitation with 6N hydrochloric acid

Sources & evidence

ORD record: ord-cee5b49821694be98ae09f1b5dc866c6
Source dataset: uspto-grants-1986_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04578522

Reaction notes

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