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

HRID 2217615

反応式

HRID 2217615 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
125 °C

実験手順

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]−.

後処理

  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

出典と根拠

ORDレコード
ord-40ab81bbc8f74ade82ab0f42e810a1c5
出典データセット
uspto-grants-2008_08
特許番号
US07407978B2

関連ノート

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