Sodium Chloride → Acetic acid, azido-, ethyl ester

HRID 1719372Notes

Reaction equation

HRID 1719372 reaction equation
Cl[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[N-:8]=[N+:9]=[N-:10].[Na+].C(Cl)Cl.[Cl-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[N:8]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N+:9]=[N-:10]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6344DichloromethaneHCID 7751Ethyl chloroacetateHCID 33557Sodium Azide

Product 1

HCID 69480Acetic acid, azido-, ethyl ester

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent2×

Procedure

A solution of 55.7 grams (0.45 moles) of 99% pure ethyl chloroacetate (Aldrich Chemical Company, Milwaukee, Wis.), 0.64 grams(1.6 millimoles) of Aliquat 336 and 30.16 grams (0.46 moles) of sodium azide (Aldrich) in 50 ml. of methylene chloride and 50 ml. of water was heated to reflux for 16 hours in a 250 ml. round bottom 3-neck flask. The mixture was allowed to cool, whereupon an additional 30 ml. of water was added to dissolve the precipitated sodium chloride. The organic phase was separated and the aqueous phase was washed twice with 10 ml. aliquots of methylene chloride. The aqueous phase was discarded and the organic phases were combined and used as a solvent for the following reaction.

Workup

  1. temperatureto reflux for 16 hours in a 250 ml
  2. temperatureto cool, whereupon an additional 30 ml
  3. customThe organic phase was separated
  4. washthe aqueous phase was washed twice with 10 ml
  5. customused as a solvent for the following reaction

Sources & evidence

ORD record
ord-9d8cd6617ec4458494a69ebfe2b048e4
Source dataset
uspto-grants-1985_09
Patent number
US04539422

Reaction notes

Loading…