4-Hydroxybenzaldehyde → HCID 23397582, Verbindung

HRID 968441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968441
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[C:12]([O:15][C@@H:16]1[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:20]([O:26][C:27](=[O:29])[CH3:28])[CH2:19][O:18][C@@H:17]1Br)(=[O:14])[CH3:13]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[C:12]([O:15][C@@H:16]1[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:20]([O:26][C:27](=[O:29])[CH3:28])[CH2:19][O:18][C@H:17]1[O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)(=[O:14])[CH3:13]

Komponenten

7

Edukt 3

HCID 1264-HydroxybenzaldehydeHCID 14798Sodium HydroxideHCID 110132022,3,4-Tri-O-acetyl-alpha-D-xylopyranosyl bromide

Produkt 1

HCID 23397582HCID 23397582, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

p-Hydroxybenzaldehyde (2.2 g, 18 mmol), dichloromethane (20 mL) and a 5% aqueous solution of sodium hydroxide (25 mL) were put in a 100 mL round bottom flask and stirred vigorously. At that time, a water phase turned yellow. To the resulting mixture, tetrabutylammonium bromide (1.0 g, 3.0 mmol) was added, and then, a dichloromethane (about 6 mL) solution of 2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide (4.0 g, 12 mmol) was added dropwise. A reaction vessel was protected from light. The resulting mixture was stirred vigorously at room temperature for 2 days. The separated organic phase was washed with 50 mL of a 5% aqueous solution of sodium hydroxide three times and then with 50 mL of water three times, dried over anhydrous sodium sulfate and evaporated to dryness to give the title compound. Light brown solid. Yield 1.5 g, 34%. The product was unstable at room temperature, and stored in the freezer.

Aufarbeitung

  1. customA reaction vessel was protected from light
  2. stirringThe resulting mixture was stirred vigorously at room temperature for 2 days
  3. washThe separated organic phase was washed with 50 mL of a 5% aqueous solution of sodium hydroxide three times
  4. dry with materialwith 50 mL of water three times, dried over anhydrous sodium sulfate
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-eb16844ebd1546b9897f4b2dcf002900
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06958389B2

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