2-Aminophenol → Carvone, (+-)-

HRID 2308171Notes

Reaction equation

HRID 2308171 reaction equation
NC1C=CC=CC=1O.[CH3:9][C:10]1[C@@H:15]([OH:16])[CH2:14][CH:13]([C:17]([CH3:19])=[CH2:18])[CH2:12][CH:11]=1>CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.[Zn+2]>[CH3:9][C:10]1[C:15](=[O:16])[CH2:14][CH:13]([C:17]([CH3:19])=[CH2:18])[CH2:12][CH:11]=1

Participants

4

Reactant 2

HCID 58012-AminophenolHCID 12233160HCID 12233160, compound

Product 1

HCID 7439Carvone, (+-)-Yield 8%

Reagents, catalysts & solvents 1

HCID 11180Zinc CaprylateCatalyst

Conditions

Temperature
213 °C

Procedure

A mixture of 1000 parts of trans-1,2-limonene oxide, 4 parts of zinc octoate (contains 18% zinc) and 2 parts of 2-aminophenol was refluxed at 200-226° C. for 3 hours in a three-necked flask equipped agitator, Dean-Stark trap, and temperature probe. After cooling 998 part of the mixture containing 67% carveol and 8% carvone was obtained. This mixture can be further processed to carvone according to example 58, or fractionated to obtain pure cis-carveol.

Workup

  1. customequipped agitator, Dean-Stark trap, and temperature probe
  2. temperatureAfter cooling 998 part of the mixture

Sources & evidence

ORD record
ord-77f264ffeaf24cafb3ec8a623539ea1e
Source dataset
uspto-grants-2004_12
Patent number
US06835686B2

Reaction notes

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