Reaktion #306956

Reaktionsgleichung

methyl 2-methyl-2′-(trifluoromethyl)biphenyl-4-carboxylate

sodium hydroxide

→

title compound

Ausbeute 84.0%

2-methyl-2′-(trifluoromethyl)biphenyl-4-carboxylic acid

Ausbeute 84.0%

Lösungsmittel

water

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated under vacuum
2. 2
   Sonstigeto give a brown solid
3. 3
   Waschenthe aqueous phase was washed twice with EtOAc (200 mL)
4. 4
   EinengenThen it was concentrated under vacuum until a precipitate
5. 5
   Sonstigewas formed (⅓ of volume)
6. 6
   FiltrationThe suspension was filtered off
7. 7
   Sonstigedried under vacuum

Vorschrift

To a solution of methyl 2-methyl-2′-(trifluoromethyl)biphenyl-4-carboxylate, prepared in step 1 (3 g; 10.19 mmol; 1 eq.) in EtOH (90 mL), was added at RT an aqueous solution of sodium hydroxide (6.12 mL; 5 M; 30.58 mmol; 3 eq.). The reaction mixture was stirred at 60° C. for one hour. The reaction mixture was concentrated under vacuum to give a brown solid. It was taken up in water (400 mL) and the aqueous phase was washed twice with EtOAc (200 mL). Aqueous phase was acidified with concentrated HCl (2 mL) to pH 2. Then it was concentrated under vacuum until a precipitate was formed (⅓ of volume). The suspension was filtered off and dried under vacuum, affording the title compound as a beige solid (2.41 g, 84%). 1H NMR: (DMSO-d6, 300 MHz) δ 13.03 (s, 1H), 7.91-7.68 (m, 5H), 7.38-7.36 (d, J=8.27 Hz, 1H), 7.27-7.25 (d, J=8.24 Hz, 1H), 2.05 (s, 3H). LC/MS (Method A): 279.0 (M−H)−. HPLC (Method A) Rt 4.49 min (Purity: 95.7%).

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