Ethyl chloroacetate → Ethyl ethoxyacetate

HRID 1953102Notes

Reaction equation

HRID 1953102 reaction equation
Cl[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-:8][CH2:9][CH3:10].[Na+]>C(O)C>[CH2:9]([O:8][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:10]

Participants

4

Reactant 2

HCID 7751Ethyl chloroacetateHCID 2723922Sodium ethoxide

Product 1

HCID 69955Ethyl ethoxyacetateYield 98.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl chloracetate (100 g, 99% pure, 0.81 mol) in ethanol is treated with ethanolic sodium ethoxide (282.9 g, 20.6% solution, 0.86 mole NaOC2H5) over a 1 hr period at 20° C.-30° C., heated at 40° C.-45° C. for 0.5 hr, cooled to room temperature, treated with diatomaceous earth, stirred for 0.25 hr and filtered. The filtercake is washed with ethanol. The combined filtrates are distilled to obtain the title product as a colorless liquid 75.78 g, 98.8% pure (71% yield), bp 87° C.-88° C./59 mmHg, identified by 13CNMR, 1HNMR and mass spectral analyses.

Workup

  1. temperatureheated at 40° C.-45° C. for 0.5 hr
  2. additiontreated with diatomaceous earth
  3. filtrationfiltered
  4. washThe filtercake is washed with ethanol
  5. distillationThe combined filtrates are distilled

Sources & evidence

ORD record
ord-6cf257fa6ac547c3a50386d55170839e
Source dataset
uspto-grants-2000_09
Patent number
US06114535

Reaction notes

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