Carbon Dioxide → HCID 86735439, compound

HRID 616043Notes

Reaction equation

HRID 616043 reaction equation
[I-].[Na+:2].[Br-].[Na+].[CH:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9]CC)=[O:8].[C:27](=[O:29])=[O:28].[C:30](#N)[CH3:31]>[Br-].C([N+](CC)(CC)CC)C>[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])([C:27]([O:29][CH2:30][CH3:31])=[O:28])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:6]([C:7]([O-:9])=[O:8])[C:12]([O:14][CH2:15][CH3:16])=[O:13].[Na+:2]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 5238Sodium IodideHCID 6342AcetonitrileHCID 790901,1,2,2-Tetraethyl 1,1,2,2-ethanetetracarboxylateHCID 253881Sodium Bromide

Product 1

HCID 86735439HCID 86735439, compound

Reagents, catalysts & solvents 1

HCID 6285Tetraethylammonium BromideCatalyst

Procedure

It will be noted that when sodium iodide, which is soluble in acetonitrile without added crown ether, is employed instead of the mixture of tetraethylammonium bromide and sodium bromide, only one of the anionic sites in substantially all the tetraethyl ethane-1,1,2,2-tetracarboxylate dianion is utilized for proton abstraction. Thus one of the anionic sites is available for reaction with carbon dioxide to yield the sodium tetraethyl ethane-1,1,1,2,2-pentacarboxylate, which precipitates in the catholyte along with the disodium 4-methyl-3,5-dioxo-6H,1,4-oxazine-2,O3 -dicarboxylate. The mixture is readily separated, however, by treatment with water.

Sources & evidence

ORD record
ord-cc774fbcdd1b40858bbe06cb587b53c3
Source dataset
uspto-grants-1978_02
Patent number
US04072583

Reaction notes

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