Oxygen → Dimethyl 2-octylmalonate

HRID 1266689Notes

Reaction equation

HRID 1266689 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH2:10]=[CH:11][CH2:12][CH2:13][CH2:14]CCC.O=O.O=[C:21]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:22][CH:23]([C:28]([O:30][CH3:31])=[O:29])[C:24]([O:26][CH3:27])=[O:25].CO[C:40]([CH:42]1[CH2:47][CH:46]([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])O[C:43]1=O)=O>C([O-])(=O)C.[Mn+2].C([O-])(=O)C.OCC([O-])=O.[Zr+4].OCC([O-])=O.OCC([O-])=O.OCC([O-])=O.C(O)(=O)C>[CH2:22]([CH:23]([C:28]([O:30][CH3:31])=[O:29])[C:24]([O:26][CH3:27])=[O:25])[CH2:21][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].[CH2:47]([CH:42]([CH2:43][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:40][CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])[CH2:46][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53]

Participants

10

Reactant 5

HCID 977OxygenHCID 7943Dimethyl malonateHCID 81251-OcteneHCID 18551906HCID 18551906, compoundHCID 18551911HCID 18551911, compound

Product 2

HCID 11728009HCID 11728009, compoundYield 6%HCID 14745592Dimethyl 2-octylmalonateYield 22%

Reagents, catalysts & solvents 3

HCID 12525Manganous AcetateCatalystHCID 57368545HCID 57368545, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 30 mmol of dimethyl malonate, 2 mmol of 1-octene, 0.04 mmol of manganese(II) acetate, 0.002 mmol of zirconium hydroxyacetate and 2 ml of acetic acid was stirred at 90° C. in an atmosphere of a gaseous mixture of nitrogen and oxygen (9:1) (1 atm=0.101 MPa) for 3 hours. The resulting reaction mixture was analyzed to find that dimethyl 2-octylmalonate (yield: 22%), dimethyl 2-(2-oxooctyl)malonate (trace amount), α-methoxycarbonyl-γ-hexyl-γ-butyrolactone (trace amount), dimethyl 2-(2-octyloctyl)malonate (yield: 6%) and dimethyl 2,2-dioctylmalonate (yield: 2%) were produced with a conversion from 1-octene of 60%.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-463825aa6dac4512be896fd7546bbaf0
Source dataset
uspto-grants-2003_04
Patent number
US06548713B2

Reaction notes

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