Hydrochloric Acid → (2E)-3-{4-[Cyclohexylidene(4-hydroxy-2-methylphenyl)methyl]phenyl}-2-propenoic acid

온도

85 °C

To a solution of ethyl (2E)-3-{4-[cyclohexylidene(4-hydroxy-2-methylphenyl)methyl]phenyl}-2-propenoate (30) (0.42 g, 1.11 mmol) in a mixture of EtOH/THF (1 mL, 4 mL) was added an aqueous solution of 5M NaOH (1.4 mL, 7.00 mmol). The mixture was stirred at 85° C. for 4 h. Upon cooling, the mixture was acidified to pH=2 with an aqueous solution of 5 M HCl. The mixture was extracted with EtOAc (1×20 mL). The organics were washed with water and brine (1×10 mL each) and dried with MgSO4. Concentration yielded 0.39 g (100%) of compound 31. 1H NMR (400 MHz, DMSO-d6): δ 1.46-1.58 (m, 6H), 1.91-1.96 (m, 2H), 1.97 (s, 3H), 2.22-2.26 (m, 2H), 6.43 (d, J=16.1 Hz, 1H), 6.53 (m, 2H), 6.83-6.85 (m, 1H), 7.08 (d, J=8.1 Hz, 2H), 7.50 (d, J=16.2 Hz, 1H), 7.55 (d, J=8.1 Hz, 2H), 9.16 (s, 1H), 12.32 (s, 1H). LCMS (ESI): m/z 349 (M+H)+.

1. temperatureUpon cooling
2. extractionThe mixture was extracted with EtOAc (1×20 mL)
3. washThe organics were washed with water and brine (1×10 mL each)
4. dry with materialdried with MgSO4
5. concentrationConcentration

ORD 기록

ord-1f6cd8ee35d04577942db09b919de06a

출처 데이터셋

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07560589B2