Butanedione → 1-Acetyl-4-adamantanone

HRID 497580Notes

Reaction equation

HRID 497580 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.C[C:13](=O)[C:14](=[O:16])C.O=O>C(O)(=O)C>[C:14]([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)(=[O:16])[CH3:13]

Participants

5

Reactant 3

HCID 650ButanedioneHCID 977OxygenHCID 64151Adamantanone

Product 1

HCID 223200001-Acetyl-4-adamantanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

In a flask were placed 2-adamantanone (100 mmol), acetylacetonatocobalt [Co(acac)2] (50 mmol), 2,3-butanedione (600 mmol), and acetic acid (100 g). A condenser and an oxygen balloon were attached to the flask, and the mixture in the flask was vigorously stirred at 80° C. for 4 hours. After the completion of the reaction, the reaction mixture was concentrated, was diluted with toluene and washing with water. The resulting organic layer was concentrated, the concentrate was subjected to silica gel column chromatography and thereby yielded the title compound 1-acetyladamantan-4-one in a yield of 21%.

Workup

  1. customIn a flask were placed
  2. customAfter the completion of the reaction
  3. concentrationthe reaction mixture was concentrated
  4. additionwas diluted with toluene
  5. washwashing with water
  6. concentrationThe resulting organic layer was concentrated

Sources & evidence

ORD record
ord-f7649be35e394dafade115bbb4284753
Source dataset
uspto-grants-2005_09
Patent number
US06949615B2

Reaction notes

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