Water → 1,1,2,2-Tetraethyl 1,1,2,2-ethanetetracarboxylate

HRID 616044Notes

Reaction equation

HRID 616044 reaction equation
[I-].[Na+].CN1C(=O)COCC1=O.[CH3:12][CH2:13][O:14][C:15]([C:17]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:16].O>C(#N)C>[CH:17]([C:29]([O:31][CH2:32][CH3:33])=[O:30])([C:15]([O:14][CH2:13][CH3:12])=[O:16])[CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium Iodide2×HCID 80313Tetraethyl ethylenetetracarboxylateHCID 936873,5-Morpholinedione, 4-methyl-

Product 1

HCID 790901,1,2,2-Tetraethyl 1,1,2,2-ethanetetracarboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Employing the apparatus and procedure described in EXAMPLE 3 above, the cathode compartment was charged with 100 milliliters of 0.3 molar sodium iodide in dry acetonitrile (dried as described in Procedure A, EXAMPLE 1 above), 2.6 grams (0.02 mole) of N-methyldiglycolimide, and 3.2 grams (0.01 mole of tetraethyl ethenetetracarboxylate and the anode compartment was charged with 30 milliliters of the 0.3 molar sodium iodide in dry acetonitrile solution. Electrolysis was conducted as described in Procedure A, EXAMPLE 1 above for 4.2 hours. Upon completion of the electrolysis, the cell was transferred to the dry box and the catholyte, containing precipitated material, was separated from the mercury pool. The solvent was evaporated in vacuo to leave a residue which was mixed with water. Evolution of gas immediately ensued and a portion of the solid material dissolved. The undissolved solid was collected by suction filtration to give a quantitative yield of tetraethyl ethane-1,1,-2,2,-tetracarboxylate. Evaporation of the filtrate in vacuo yielded 2.03 grams (52 percent) of sodium N-methyldiglycolimide-3-carboxylate.

Workup

  1. customas described in Procedure A, EXAMPLE 1 above for 4.2 hours
  2. additionthe catholyte, containing
  3. customprecipitated material
  4. customwas separated from the mercury pool
  5. customThe solvent was evaporated in vacuo
  6. customto leave a residue which
  7. dissolutiona portion of the solid material dissolved
  8. filtrationThe undissolved solid was collected by suction filtration

Sources & evidence

ORD record
ord-8067bae7830e424bb8ec8430e75cd6ed
Source dataset
uspto-grants-1978_02
Patent number
US04072583

Reaction notes

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