Hydrochloric Acid → Z-3-(3,5-Dimethoxyphenyl)-2-(4-hydroxyphenyl)-acrylic acid

HRID 2238250

반응식

HRID 2238250 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:11]=[C:12](\[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)/[C:13]([OH:15])=[O:14])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.COC1C=C(C=C(C2C=CC(O)=CC=2)C(O)=O)C=C(OC)C=1.C(OC(=O)C)(=O)C.C(N(CC)CC)C.Cl>C(OCC)(=O)C>[CH3:10][O:9][C:7]1[CH:6]=[C:5](/[CH:11]=[C:12](/[C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)\[C:13]([OH:15])=[O:14])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 3567513-(3,5-Dimethoxyphenyl)-2-(4-hydroxyphenyl)-acrylic acidHCID 9857492HCID 9857492, 화합물

생성물 1

HCID 5386532Z-3-(3,5-Dimethoxyphenyl)-2-(4-hydroxyphenyl)-acrylic acid

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
125 °C

실험 절차

E-3-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)-acrylic acid, 7 (10.0 g, 33.3 mmol) was dissolved in a mixture of acetic anhydride (40 mL, 0.42 mole) and triethylamine (40 mL, 0.29 mole) and heated at 125° C. for 24 h. The mixture was cooled to room temperature. Ethyl acetate (150 mL) was added, further cooled to 5° C., acidified with concentrated HCl (30 mL) and stirred at this temperature for 90 min. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were washed with water (2×50 mL) and extracted with aqueous NaOH (5M, 3×70 mL). The aqueous alkaline layer was acidified with glacial acetic acid (65 mL) to pH 5.2 and stirred at 0° C. for 30 min. Solid that separated was filtered and mother liquor was acidified with concentrated HCl (90 mL) and stirred at 5° C. for 1 h. Solid that separated was filtered, washed with cold water (2×50 mL) and dried at 45° C. for 6 h to yield, 19, (1.3 g, 13%): mp 135-137° C.; 1HNMR (400 MHz, DMSO-d6) δ 13.28 (br, 1H), 9.70 (br, 1H), 7.32. (d, J=10.4 Hz, 2H), 6.81 (s, 1H, overlapped), 6.79 (d, J=9.7 Hz, 2H), 6.67 (d, J=2.5 Hz, 2H), 6.64 (t, J=2.5 Hz, 1H), and 3.73 (s, 6H); MS (EI) m/z 299[M]−.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. temperaturefurther cooled to 5° C.
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (100 mL)
  5. washThe combined organic layers were washed with water (2×50 mL)
  6. extractionextracted with aqueous NaOH (5M, 3×70 mL)
  7. stirringstirred at 0° C. for 30 min
  8. customSolid that separated
  9. filtrationwas filtered
  10. stirringstirred at 5° C. for 1 h
  11. customSolid that separated
  12. filtrationwas filtered
  13. washwashed with cold water (2×50 mL)
  14. customdried at 45° C. for 6 h
  15. customto yield

출처 및 근거

ORD 기록
ord-4496fcf352b949b7ae4474b4de78f2d5
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718682B2

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