Acetic Acid → 3-Oxo-alpha-ionone

HRID 1074645

Reaction equation

HRID 1074645 reaction equation
[CH3:1][C:2]1[CH:7](/[CH:8]=[CH:9]/[C:10]([CH3:12])=[O:11])[C:6]([CH3:14])([CH3:13])[CH2:5][CH2:4][CH:3]=1.[Br-].[NH4+].C(O)(=[O:19])C>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.C1CCCCC1>[CH3:1][C:2]1[CH:7](/[CH:8]=[CH:9]/[C:10](=[O:11])[CH3:12])[C:6]([CH3:14])([CH3:13])[CH2:5][C:4](=[O:19])[CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 25514Ammonium BromideHCID 5282108Alpha-Ionone2×

Product 1

HCID 53636853-Oxo-alpha-ionone

Reagents, catalysts & solvents 2

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 8078CyclohexaneSolvent

Procedure

Items 1-6 given in Table 1 hereinafter are carried out following the procedure of Example 1 substituting therein 5 g of 92% α-ionone for the 40 g of 98% α-ionone, 1.3 g (20 mol percent) of cobalt acetate tetrahydrate for the 10.4 g, and 0.7 g, (27 mol percent) of ammonium bromide for the 4.0 g. The amount of solvent substituting for glacial acetic acid and cyclohexane is represented in Table 1 and amounts to 60 ml. The yields of 3,5,5-trimethyl-4-[(E)-3-oxo-1-butenyl]-2-cyclohexen-1-one (3-oxo-α-ionone) are determined by gas chromatography (GC). It will be observed that the sum of all products appearing in the gas chromatogram only amounts to a maximum of about 60% of the total weight. The remainder probably consists of oligomeric by-products. The oxidation conditions are not optimized.

Sources & evidence

ORD record
ord-792a6b9d0d4b4b698db31596822e5214
Source dataset
uspto-grants-1983_07
Patent number
US04393243

Linked notes

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