Formate → Ethyl nitroacetate

HRID 2351583Notes

Reaction equation

HRID 2351583 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].[OH-].[K+].C([C:9]([O:11][CH2:12][CH3:13])=[O:10])#N.C([O-])=O.Cl>CS(C)=O>[N+:1]([CH2:4][C:9]([O:11][CH2:12][CH3:13])=[O:10])([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 283FormateHCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 14797Potassium HydroxideHCID 69336Ethyl cyanoformate

Product 1

HCID 69379Ethyl nitroacetateYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a 100 ml three necked round bottom flask, equipped with a liquid addition funnel, a solid addition funnel and a condenser topped with a nitrogen inlet, was added 20 ml of dimethylsulfoxide and 1.08 g (0.0178 mole) nitromethane. 0.1 g (0.00178 mole) potassium hydroxide followed by 1 ml of a 20% solution of ethyl cyanoformate in (0.0021 mle) dimethylsulfoxide. The solution was stirred for a short period and the addition of each reactant (base and formate) was repeated nine times. The resultant solution remained homogeneous throughout the addition process, was stirred at ambient temperature for one hour and then acidified to pH of 4 with conc. hydrochloric acid. The product was extracted with ethyl acetate and dried with anhydrous magnesium sulfate. The magnesium sulfate was filtered off and solvent evaporated to give ethyl nitroacetate in 68% yield.

Workup

  1. customtopped with a nitrogen inlet
  2. stirringwas stirred at ambient temperature for one hour
  3. extractionThe product was extracted with ethyl acetate
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationThe magnesium sulfate was filtered off
  6. customsolvent evaporated

Sources & evidence

ORD record
ord-3016f1727b1144e08576e12dc11a3b65
Source dataset
uspto-grants-1989_10
Patent number
US04873358

Reaction notes

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