Perillaldehyde → Perilla alcohol

HRID 1604756

Reaction equation

HRID 1604756 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 369312Perilla alcohol

Reagents, catalysts & solvents 1

HCID 10219390chromium (VI) trioxideCatalyst

Procedure

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.

Workup

  1. customto yield various oxidation products
  2. customOnce isolated

Sources & evidence

ORD record
ord-efc8b7b2544149a1a9a6fdf90618994b
Source dataset
uspto-grants-1999_11
Patent number
US05994598

Linked notes

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