Hydrochloric Acid → (2E)-3-{4-[(3-Chloro-4-hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}-2-propenoic acid

온도

60 °C

To a solution of ethyl (2E)-3-{4-[(3-chloro-4-hydroxyphenyl)(3,3,5,5-tetramethyl cyclohexylidene)methyl]phenyl}-2-propenoate (128) (0.26 g, 0.57 mmol) in a mixture of EtOH (6 mL) and THF (6 mL) was added an aqueous solution of 1 N NaOH (7 mL). The mixture was stirred at 60° C. for 2 h. Upon cooling, the mixture was acidified to pH=2 with an aqueous solution of 2 N HCl. The mixture was extracted with EtOAc (2×50 mL). The combined organic extract was washed with brine and dried over Na2SO4. Upon concentration and adding hexanes, the title compound 129 was obtained as light yellow foam (0.24 g, 99%). mp 111-114° C. 1H NMR (400 MHz, DMSO-d6): δ 0.86 (s, 6H), 0.88 (s, 6H), 1.25 (s, 2H), 1.87 (s, 2H), 1.90 (s, 2H), 6.45 (d, J=15.9 Hz, 1H), 6.80-6.95 (m, 2H), 7.06 (s, 1H), 7.16 (d, J=7.7 Hz, 2H), 7.53 (d, J=15.9 Hz, 1H), 7.59 (d, J=7.5 Hz, 2H), 10.08 (s, 1H), 12.33 (s, 1H). LCMS (ESI): m/z 423 (M−H)−. Anal. Calcd for C26H29ClO3: C, 73.48; H, 6.88; Found: C, 73.18; H, 7.06.

1. temperatureUpon cooling
2. extractionThe mixture was extracted with EtOAc (2×50 mL)
3. extractionThe combined organic extract
4. washwas washed with brine
5. dry with materialdried over Na2SO4
6. concentrationUpon concentration
7. additionadding hexanes

ORD 기록

ord-077e8502764b4cb386d8768253e9f9e8

출처 데이터셋

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07799828B2