Hydrochloric Acid → 2-Ethoxy-3-oxo-succinic acid diethyl ester

HRID 1422191Notes

Reaction equation

HRID 1422191 reaction equation
[Na].C(O)C.[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8][CH2:9][CH3:10])=O.C([O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])C.Cl>C1(C)C=CC=CC=1>[CH2:9]([O:8][CH:6]([C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:17])[C:5]([O:12][CH2:13][CH3:14])=[O:11])[CH3:10]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7268Diethyl OxalateHCID 69955Ethyl ethoxyacetateHCID 5360545Sodium

Product 1

HCID 111389942-Ethoxy-3-oxo-succinic acid diethyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

A stirred mixture of molten sodium metal (24.15 g, 1.05 mol) in toluene is treated with ethanol (55.2 g, 1.2 mol) over a 1 hr period at 100° C.-110° C., heated at reflux temperatures for 0.5 hr, cooled to 45° C., treated with a mixture of diethyl oxalate (160.6 g, 1.1 mol) and ethyl ethoxyacetate (132 g, 98%, 0.98 mol) over a 1 hr period at 45° C.-50° C., heated at 55° C.-60° C. for 1.5 hr and poured into 328 g of 14% HCl with cooling. The resultant mixture is separated. The title product is obtained as a 32% solution in the organic phase, identified by HRGC analysis, total yield is 198.2 g (87% yield).

Workup

  1. temperatureheated
  2. temperatureat reflux temperatures for 0.5 hr
  3. temperatureheated at 55° C.-60° C. for 1.5 hr
  4. temperaturewith cooling
  5. customThe resultant mixture is separated

Sources & evidence

ORD record
ord-64905c3ea2614cef833c6124221a1510
Source dataset
uspto-grants-2000_06
Patent number
US06080867

Reaction notes

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