Diethyl Oxalate → Ethanedioic acid, 1-ethyl ester, potassium salt (1:1)

HRID 3963

Reaction equation

HRID 3963 reaction equation
[C:1]([O:8]CC)(=[O:7])[C:2]([O:4][CH2:5][CH3:6])=[O:3].C[Si](C)(C)[O-].[K+:16]>CCOCC>[C:2]([O:4][CH2:5][CH3:6])(=[O:3])[C:1]([O-:8])=[O:7].[K+:16]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 23668039Potassium trimethylsilanolate

Product 1

HCID 23678856Ethanedioic acid, 1-ethyl ester, potassium salt (1:1)Yield 79.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The procedure of Example 1 was followed using diethyl oxalate (3.0 mL, 22 mmol), potassium trimethylsilanolate (3.85 g, 22 mmol), dry ether (70 mL), an ice bath to maintain room temperature initially, and a 1.5 h reaction time. Potassium ethyl oxalate (2.72 g, 79% yield) was isolated as a white solid: 1H NMR (D2O) δ 1.3 (t, J=7.2 Hz, CH3, 3H), 4.2 ppm (q, J=7.2 Hz, CH2, 2H). Anal. Calcd. for C4H5KO4 : C, 30.76; H, 3.23; K, 25.04. Found: C, 30.39; H, 3.29; K, 25.30.

Workup

  1. customa 1.5 h reaction time

Sources & evidence

ORD record
ord-47f7fab3590a4b288fe5c9f9e0c471c5
Source dataset
uspto-grants-1988_02
Patent number
US04723016

Linked notes

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