Butanedione → Adamantane

HRID 1699149Notes

Reaction equation

HRID 1699149 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:11](C(C)=O)([CH3:13])=[O:12]>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C(O)(=O)C>[C:11]([C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2)(=[O:12])[CH3:13].[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 2

HCID 650ButanedioneHCID 9238Adamantane

Product 2

HCID 9238AdamantaneHCID 123126Methyl tricyclo(3.3.1.13,7)dec-1-yl ketone

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.3 mol of adamantane, 1.8 mol of biacetyl, 1.5 mmol of cobalt (II) acetate, and 300 ml of acetic acid was stirred at 60° C. under an oxygen atmosphere (1 atm) for 4 hours. The reaction mixture was concentrated to about 20% by weight, extracted with ethyl acetate, dried and washed with hexane to give 1-acetyladamantane in yield of 52% at a conversion rate from adamantane of 87%.

Workup

  1. concentrationThe reaction mixture was concentrated to about 20% by weight
  2. extractionextracted with ethyl acetate
  3. customdried
  4. washwashed with hexane

Sources & evidence

ORD record
ord-3c8431907c564a7fb62518fb450ff338
Source dataset
uspto-grants-2002_02
Patent number
US06344590B1

Reaction notes

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