Reaktion #306977

Reaktionsgleichung

methyl 4-(4-methyl-3-thienyl)-3-(trifluoromethyl)benzoate

sodium hydroxide

→

title compound

Ausbeute 90.9%

4-(4-methyl-3-thienyl)-3-(trifluoromethyl)benzoic acid

Ausbeute 90.9%

Lösungsmittel

water

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated
2. 2
   Sonstigeto give a brown solid which
3. 3
   Waschenthe aqueous phase was washed twice with EtOAc
4. 4
   Extraktionextracted with EtOAc (250 mL)
5. 5
   TrocknenThe organic layer was dried over MgSO4
6. 6
   Einengenconcentrated

Vorschrift

A solution of methyl 4-(4-methyl-3-thienyl)-3-(trifluoromethyl)benzoate (3 g; 9.99 mmol; 1 eq.) in EtOH (90 mL) at RT was treated with sodium hydroxide (5.99 mL; 5 M; 29.97 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 and extracted with EtOAc (250 mL). The organic layer was dried over MgSO4 and concentrated affording the title compound as a brown oil (2.60 g, 90%). 1H NMR (DMSO-d6, 300 MHz) δ 13.07 (br s, 1H), 8.34-8.24 (m, 2H), 7.57-7.54 (m, 1H), 7.47-7.46 (m, 1H), 7.34-7.33 (m, 1H), 1.98 (s, 3H). LC/MS (Method A): 284.9 (M−H)−. HPLC (Method A) Rt 4.53 min (Purity: 95.5%).

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