N,N-Dimethylaniline → Resveratrol

HRID 1760826

Reaktionsgleichung

Reaktionsgleichung von HRID 1760826
[Cl-].[Al+3].[Cl-].[Cl-].CN(C)C1C=CC=CC=1.C([O:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]2[CH:35]=[C:34]([O:36]CC3C=CC=CC=3)[CH:33]=[C:32]([O:44]CC3C=CC=CC=3)[CH:31]=2)=[CH:24][CH:23]=1)C1C=CC=CC=1>ClCCl>[OH:36][C:34]1[CH:35]=[C:30](/[CH:29]=[CH:28]/[C:25]2[CH:26]=[CH:27][C:22]([OH:21])=[CH:23][CH:24]=2)[CH:31]=[C:32]([OH:44])[CH:33]=1

Komponenten

5

Edukt 3

HCID 949N,N-DimethylanilineHCID 6451240Aluminum(III) ChlorideHCID 10217778(E)-3,5,4'-Tribenzyloxystilbene

Produkt 1

HCID 445154ResveratrolAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Into a 3 lit. round-bottomed flask equipped with a thermometer were added aluminum chloride (390.35 gm) and N,N-dimethylaniline (413.10 gm) maintaining the temperature at 40-50° C. To this solution, a solution of (E)-1-(4-(benzyloxy)phenyl)-2-(3,5-bis(benzyloxy)phenyl)ethene (243 gm) prepared according to example 1 in dichloromethane was added and stirred well. After the reaction was over, the reaction mixture was acidified, extracted into ethyl acetate and concentrated to get pure (E)1-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)ethene (E-Resveratrol) in the exclusive E- form in 90% yield. 1H NMR (DMSO-d6, Bruker 400 MHz Avarice): δ 6.11 (t, J=1.8 Hz), 6.38 (d, J=1.8 Hz, 2H), 6.75 (d, J=8.5 Hz, 2H), 6.82 (d, J=16.3 Hz, 1H), 6.92 (d, J=16.3 Hz), 7.39 (d, J=8.4 Hz, 2H); Mass m/e: 228.2.

Aufarbeitung

  1. customInto a 3 lit. round-bottomed flask equipped with a thermometer
  2. additionwas added
  3. extractionextracted into ethyl acetate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e4d481f4fc5547caa6275d9875f4fe72
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06844471B2

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