Hydroxyphenylacetic acid → 3-(3,5-Dimethoxyphenyl)-2-(4-hydroxyphenyl)-acrylic acid

HRID 2217602

Reaktionsgleichung

Reaktionsgleichung von HRID 2217602
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:6]=O.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][CH:15]=1.C(OC(=O)C)(=O)C.C(N(CC)CC)C.Cl>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([OH:13])=[CH:15][CH:16]=2)[C:21]([OH:23])=[O:22])[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1

Komponenten

6

Edukt 5

HCID 127Hydroxyphenylacetic acidHCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 817473,5-Dimethoxybenzaldehyde

Produkt 1

HCID 3567513-(3,5-Dimethoxyphenyl)-2-(4-hydroxyphenyl)-acrylic acidAusbeute 47 %

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

To a mixture of 3,5-dimethoxybenzaldehyde, 5, (500 g, 3.0 mol) and 4-hydroxyphenyl acetic acid, 6, (457 g, 3.0 mol) was added acetic anhydride (1.0 L, 10.60 mole) and triethylamine (420 mL, 3.0 mol). After stirring at 130-140° C. for 6 h, the mixture was cooled to room temperature. Concentrated HCl (1 L) was added to the reaction mixture slowly over 50 min while keeping the temperature between 20-30° C. The light yellow precipitate obtained was filtered and washed with water. The solid was dissolved in 3N NaOH (5 L) and stirred for 1 h and filtered. The filtrate was acidified to pH 1 with concentrated HCl while maintaining a temperature at 25-30° C. The precipitated product was filtered and washed with water to give crude product that was recrystallized from MeOH—H2O and dried at 40° C. for 6 h to yield 7 (428 g, 47%): mp 225-227° C. (lit. 226-228° C.)17; 1HNMR (360 MHz, DMSO-d6) δ 12.48 (br s, 1H), 9.42 (s, 1H), 7.59 (s, 1H), 6.95 (d, J=8.0 Hz, 2H), 6.76 (d, J=8.0 Hz, 2H), 6.35 (t, J=2.2 Hz, 1H), 6.27 (d, J=2.2 Hz, 2H), 3.56 (s, 6H); MS (EI) m/z 299[M]−.

Aufarbeitung

  1. temperaturethe mixture was cooled to room temperature
  2. custombetween 20-30° C
  3. customThe light yellow precipitate obtained
  4. filtrationwas filtered
  5. washwashed with water
  6. dissolutionThe solid was dissolved in 3N NaOH (5 L)
  7. stirringstirred for 1 h
  8. filtrationfiltered
  9. temperaturewhile maintaining a temperature at 25-30° C
  10. filtrationThe precipitated product was filtered
  11. washwashed with water
  12. customto give crude product that
  13. customwas recrystallized from MeOH—H2O
  14. customdried at 40° C. for 6 h

Quellen und Nachweise

ORD-Eintrag
ord-0633be93746340a58a2ea05833b79927
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07407978B2

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