Oxygen → Adamantanone

HRID 1019284Notes

Reaction equation

HRID 1019284 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.[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

Participants

6

Reactant 3

HCID 977OxygenHCID 10665N-HydroxyphthalimideHCID 64151Adamantanone

Product 2

HCID 64151AdamantanoneHCID 64184Idramantone

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)3, and 250 ml of acetic acid was stirred at 85° C. in an oxygen atmosphere (1 atm) for 10 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 of the following formula in a yield of 48% with a conversion rate from 2-adamantanone of 74%.

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-704e04f58472498aaa00033edb7f6d8e
Source dataset
uspto-grants-2002_11
Patent number
US06486330B1

Reaction notes

Loading…