Hydrochloric Acid → Diethyl ethoxypropanedioate

HRID 628971Notes

Reaction equation

HRID 628971 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=O)[C:2]([O:4][CH2:5][CH3:6])=[O:3].C(OC[C:15]([O:17][CH2:18][CH3:19])=[O:16])C.[O-]CC.[Na+].Cl>C1(C)C=CC=CC=1>[CH2:18]([O:17][C:15](=[O:16])[CH:1]([O:8][CH2:9][CH3:10])[C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 69955Ethyl ethoxyacetateHCID 2723922Sodium ethoxide

Product 1

HCID 12196926Diethyl ethoxypropanedioateYield 93.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of diethyl oxalate (39.23 ml, 1.12 eq.) and ethyl ethoxyacetate (34.95 ml, 1 eq.) was added dropwise to a slurry of sodium ethoxide (18.64 g, 1.07 eq.) in toluene (100 ml) at 45-50° C. After dropping, the resulting solution was heated to 70-80° C. for 2 hrs and poured into 70 ml of 14% HCl with cooling. The resultant mixture was extracted with EA and the combined organic layers were washed with brine and dried in vacuo to give 55.86 g (93.7%) of a product.

Workup

  1. temperaturewith cooling
  2. extractionThe resultant mixture was extracted with EA
  3. washthe combined organic layers were washed with brine
  4. customdried in vacuo

Sources & evidence

ORD record
ord-708b5a7b3f224339a01f5d46156bbe53
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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