Potassium Hydroxide → 2-Methyl-2-[4-(trifluoromethyl)phenyl]propanoic acid

Temperature

23 °C

A solution of methyl 2-methyl-2-(4-(trifluoromethyl)phenyl)propanoate (1528 mg, 6206 μmol) in MeOH (60 mL) and water (15 mL), was treated with KOH (1741 mg, 31028 μmol). The reaction was heated to reflux. After 18 hours, the reaction was cooled to 23° C. and concentrated in vacuo. The crude mixture was partitioned between water/diethyl ether (100 mL each). The aqueous layer was separated and washed with diethyl ether (100 mL). The combined ether layers were extracted with a 1N NaOH solution (25 mL). The combined aqueous washes were acidified with concentrated HCl to pH=2 and were then extracted with EtOAc (3×100 mL). The combined EtOAc layers were dried over MgSO4 and concentrated in vacuo to afford 1323 mg of the title compound. MS m/e=233.1 (M+H)+.

1. temperatureThe reaction was heated to reflux
2. concentrationconcentrated in vacuo
3. customThe crude mixture was partitioned between water/diethyl ether (100 mL each)
4. customThe aqueous layer was separated
5. washwashed with diethyl ether (100 mL)
6. extractionThe combined ether layers were extracted with a 1N NaOH solution (25 mL)
7. extractionwere then extracted with EtOAc (3×100 mL)
8. dry with materialThe combined EtOAc layers were dried over MgSO4
9. concentrationconcentrated in vacuo

ORD record

ord-c1dfacb81d5e4edd81e157e5d2cf3afe

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07635715B2