Benzaldehyde → HCID 11032680, Verbindung

HRID 1357492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1357492
[CH2:1]1[C@@H:6](O)[C@@H:5]([OH:8])[C@H:4]([OH:9])[CH2:3][C@@:2]1([C:11]([OH:13])=[O:12])[OH:10].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[OH:10][C@@:2]12[CH2:1][C@@H:6]([O:13][C:11]1=[O:12])[C@H:5]1[C@H:4]([O:9][CH:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:8]1)[CH2:3]2

Komponenten

5

Edukt 3

HCID 240BenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 178524980HCID 178524980, Verbindung

Produkt 1

HCID 11032680HCID 11032680, VerbindungAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

The procedure in J. Org. Chem. 1995, 50, 888-890 was followed. Briefly, a solution of quinic acid (20.0 g, 0.104 mol), benzaldehyde (16.6 g, 156 mmol) and para-toluenesulfonic acid monohydrate (1.0 g, 5.26 mmol) in toluene (350 mL) was refluxed for 10 hours in a flask equipped with a Dean-Stark trap. The reaction mixture was cooled, washed with saturated NaHCO3 solution and brine, dried (MgSO4). Filtered and concentrated. The concentrate was dissolved in 1:1 hexanes/ethyl acetate (100 mL) and cooled to −20° C. for 2 hours to provide 10.8 g (40%) of the desired product.

Aufarbeitung

  1. customequipped with a Dean-Stark trap
  2. temperatureThe reaction mixture was cooled
  3. washwashed with saturated NaHCO3 solution and brine
  4. dry with materialdried (MgSO4)
  5. filtrationFiltered
  6. concentrationconcentrated
  7. dissolutionThe concentrate was dissolved in 1:1 hexanes/ethyl acetate (100 mL)

Quellen und Nachweise

ORD-Eintrag
ord-47e21702ef964b9caccb3deb3006df99
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593314B1

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