Chloroform → Dimethylaminoethyl acetate

HRID 223268Notes

Reaction equation

HRID 223268 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH3:8][N:9](C)[CH2:10]CO.C(Cl)(Cl)Cl.[OH-].[Na+]>C(O)(=O)C>[N:9]([CH2:2][CH2:1][O:4][C:5]([CH3:6])=[O:7])([CH3:10])[CH3:8]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 79022-(Dimethylamino)ethanolHCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide

Product 1

HCID 15013Dimethylaminoethyl acetateYield 77.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

With gentle cooling, 168.5 g of acetic anhydride are added dropwise to 133.6 g of 2-dimethylaminoethanol in the course of 20 minutes, whereupon the temperature rises from 20° C. to a maximum of 105° C. The reaction mixture is kept for 30 minutes at 100° C. and then cooled. Then 750 ml of CHCl3 are added and the acetic acid formed is neutralised with 380 ml of 20% sodium hydroxide solution at 30°-35° C. with cooling. The two phases are separated and the organic phase is washed with a small amount of H2O. Distillation of the residue affords 151.7 g (77.7%) of product with a boiling point of 114° C./225 torr.

Workup

  1. customrises from 20° C. to a maximum of 105° C
  2. temperaturecooled
  3. temperaturewith cooling
  4. customThe two phases are separated
  5. washthe organic phase is washed with a small amount of H2O
  6. distillationDistillation of the residue

Sources & evidence

ORD record
ord-6e2f63de7caf4968917a2c4eb49a9f8c
Source dataset
uspto-grants-1982_10
Patent number
US04352913

Reaction notes

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