Butanedione → HCID 13225184, compound

HRID 2302103Notes

Reaction equation

HRID 2302103 reaction equation
[C:1]([C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2)([OH:3])=[O:2].[C:14]([C:17]([CH3:19])=[O:18])([CH3:16])=[O:15].[OH:20]N1C(=O)C2=CC=CC=C2C1=O>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C(O)(=O)C>[C:14]([C:10]12[CH2:12][CH:6]3[CH2:7][CH:8]([CH2:13][C:4]([C:1]([OH:3])=[O:2])([CH2:5]3)[CH2:11]1)[CH2:9]2)(=[O:15])[CH3:16].[C:17]([C:14]12[CH2:12][C:6]3([OH:20])[CH2:7][CH:8]([CH2:13][C:4]([C:1]([OH:3])=[O:2])([CH2:5]3)[CH2:16]1)[CH2:9]2)(=[O:18])[CH3:19]

Participants

7

Reactant 3

HCID 650ButanedioneHCID 10665N-HydroxyphthalimideHCID 132351-Adamantanecarboxylic acid2×

Product 2

HCID 13225184HCID 13225184, compoundYield 46%HCID 18463112HCID 18463112, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3 mmol of 1-carboxyadamantane, 18 mmol of biacetyl, 0.3 mmol of N-hydroxyphthalimide, 0.015 mmol of cobalt (II) acetate, and 3 ml of acetic acid was stirred at 75° C. under an oxygen atmosphere (1 atm) for 6 hours. Gas chromatographic analysis of products in the reaction mixture demonstrated that 1-carboxyadamantane was converted, at a rate of 92%, to 1-acetyl-3-carboxyadamantane (yield 46%), and 1-acetyl-3-carboxy-5-adamantanol (yield 24%).

Sources & evidence

ORD record
ord-94515756bd5b43ca9e1678893da992bf
Source dataset
uspto-grants-2002_08
Patent number
US06429314B1

Reaction notes

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