Benzaldehyde → HCID 69497995, Verbindung

HRID 495320

Reaktionsgleichung

Reaktionsgleichung von HRID 495320
[C:1]1(=[O:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:7].[Na+].[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1>C(O)C.O>[O:7]1[CH2:5][CH2:4][CH2:3][CH2:2][CH:1]1[O:6][C:13]1[CH:14]=[CH:15][C:10]([CH:9]=[C:2]2[CH2:3][CH2:4][C:5](=[CH:28][C:27]3[CH:30]=[CH:31][C:24]([O:23][CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][O:17]4)=[CH:25][CH:26]=3)[C:1]2=[O:6])=[CH:11][CH:12]=1

Komponenten

7

Edukt 4

HCID 240BenzaldehydeHCID 8452CyclopentanoneHCID 14798Sodium HydroxideHCID 112527364-(2-Tetrahydro-2H-pyranoxy)benzaldehyde

Produkt 1

HCID 69497995HCID 69497995, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

Cyclopentanone (8.8 ml, 0.099 mol) was dissolved in ethanol (12 ml) and added to NaOH dissolved in water (25 ml) and ethanol (7 ml), and was left to stir for 25 min. This was then added to the THP protected benzaldehyde from 1CW01 (46.12 g, 0.22 mol), and the mixture was left to stir at room temperature for approximately 16 hours. A solid precipitate was isolated by vacuum filtration, washed with water (2×50 ml) and then ethanol (4×40 ml). This solid was recrystallised from ethanol to give a yellow solid (33.74 g, 74%).

Aufarbeitung

  1. additionThis was then added to the THP
  2. waitthe mixture was left
  3. stirringto stir at room temperature for approximately 16 hours
  4. customA solid precipitate was isolated by vacuum filtration
  5. washwashed with water (2×50 ml)
  6. customThis solid was recrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-0dc7a94483894b17b716ed6beacbeb41
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06939479B2

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