2-Aminophenol → Carvone, (+-)-

HRID 2308170Notes

Reaction equation

HRID 2308170 reaction equation
[CH3:1][C:2]([C@H:4]1[CH2:9][C@H:8]2[O:10][C@@:7]2([CH3:11])[CH2:6][CH2:5]1)=[CH2:3].NC1C=CC=CC=1O.CC1[C@@H](O)CC(C(C)=C)CC=1>CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.[Zn+2]>[CH3:11][C:7]1[C:8](=[O:10])[CH2:9][CH:4]([C:2]([CH3:3])=[CH2:1])[CH2:5][CH:6]=1

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 449290(+)-trans-Limonene oxideHCID 12233160HCID 12233160, compound

Product 1

HCID 7439Carvone, (+-)-Yield 3%

Reagents, catalysts & solvents 1

HCID 11180Zinc CaprylateCatalyst

Conditions

Temperature
212.5 °C

Procedure

A mixture of 1000 parts of cis-1,2-limonene oxide, 1 part of zinc octoate (contains 18% zinc) and 0.5 parts of 2-aminophenol was refluxed at 200-225° C. for 1.5 hours in a three-necked flask equipped agitator, Dean-Stark trap, and temperature probe. This process is exothermic. Cooling should be applied to prevent a runaway reaction. After cooling 998 part of the mixture containing 87% carveol and 3% carvone was obtained. This mixture can be further processed to carvone according to example 58, or fractionated to obtain pure trans-carveol.

Workup

  1. customequipped agitator, Dean-Stark trap, and temperature probe
  2. temperatureCooling should
  3. customa runaway reaction
  4. temperatureAfter cooling 998 part of the mixture

Sources & evidence

ORD record
ord-c1040606167946c69cb56b7d2163fdd7
Source dataset
uspto-grants-2004_12
Patent number
US06835686B2

Reaction notes

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