Ethyl chloroacetate → Ethyl ethoxyacetate

HRID 582806

Reaction equation

HRID 582806 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

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-bf0c80d3ebdd46919339dbf745980f16
Source dataset
uspto-grants-1999_07
Patent number
US05925764

Linked notes

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