Oxygen → Idramantone

HRID 1976925Notes

Reaction equation

HRID 1976925 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[O:11])[CH2:8]2.[OH:12]N1C(=O)C2=CC=CC=C2C1=O.O=O>C(O)(=O)C>[OH:12][C:7]12[CH2:9][CH:3]3[CH2:4][CH:5]([CH2:10][CH:1]([C:2]3=[O:11])[CH2:8]1)[CH2:6]2

Participants

5

Reactant 3

HCID 977OxygenHCID 10665N-HydroxyphthalimideHCID 64151Adamantanone

Product 1

HCID 64184IdramantoneYield 37%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.1 mol of 2-adamantanone, 10 mmol of N-hydroxyphthalimide, 0.33 mmol of acetylacetonatovanadium V(AA)3, 0.17 mmol of acetylacetonatomanganese Mn(AA)2, and 250 ml of acetic acid was stirred at 80° C. in an oxygen atmosphere (1 atm) for 6 hours. The resulting reaction mixture was concentrated and was then extracted with ethyl acetate. A portion of an organic layer was concentrated and was then cooled for crystallization to yield 5-hydroxy-2-adamantanone (yield: 37%). The conversion rate from 2-adamantanone was 64%.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated
  3. extractionwas then extracted with ethyl acetate
  4. concentrationA portion of an organic layer was concentrated
  5. temperaturewas then cooled for crystallization

Sources & evidence

ORD record
ord-4b76eb282bea455ab976bd83e88944e0
Source dataset
uspto-grants-2001_05
Patent number
US06229050B1

Reaction notes

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