Perillaldehyde → Perilla alcohol

HRID 1604756

Reaktionsgleichung

Reaktionsgleichung von HRID 1604756
CC1CC[C@@H](C(C)=C)CC=1.[Se](=O)=O.[CH3:14][C:15]([CH:17]1[CH2:22][CH:21]=[C:20]([CH:23]=[O:24])[CH2:19][CH2:18]1)=[CH2:16]>[O-2].[O-2].[O-2].[Cr+6]>[CH3:16][C:15]([C@@H:17]1[CH2:18][CH:19]=[C:20]([CH2:23][OH:24])[CH2:21][CH2:22]1)=[CH2:14]

Komponenten

5

Edukt 3

HCID 16441Perillaldehyde2×HCID 24007Selenium DioxideHCID 440917(+)-Limonene

Produkt 1

HCID 369312Perilla alcohol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10219390chromium (VI) trioxideKatalysator

Versuchsvorschrift

Perillyl alcohol can be produced by reacting limonene with selenium dioxide (that is toxic) and other oxidants (that are difficult to work with i.e., anhydrous chromium trioxide) to yield various oxidation products, including a small amount of perillaldehyde. Once isolated, perillaldehyde is reduced to afford perillyl alcohol. While this two-step process is conceptually attractive, the oxidation of limonene to give perillyl alcohol proceeds in a low overall yield.

Aufarbeitung

  1. customto yield various oxidation products
  2. customOnce isolated

Quellen und Nachweise

ORD-Eintrag
ord-efc8b7b2544149a1a9a6fdf90618994b
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05994598

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