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

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-86060368b87541c79539514155072b2d

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928139B2