Potassium Carbonate → Ethyl 2,4-dinitro-5-chlorophenoxyacetate

HRID 1381633Notes

Reaction equation

HRID 1381633 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+].COCCOCCN(CCOCCOC)CCOCCOC>C(#N)C.Cl>[N+:12]([C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[C:6]([Cl:8])=[CH:7][C:2]=1[O:17][CH2:16][C:15]([O:19][CH2:20][CH3:21])=[O:18])([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 12184Ethyl GlycolateHCID 772861,3-Dichloro-4,6-dinitrobenzeneHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-

Product 1

HCID 14423666Ethyl 2,4-dinitro-5-chlorophenoxyacetateYield 73.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 1,5-dichloro-2,4-dinitrobenzene (2.0 g), ethyl glycolate (1.32 g) and anhydrous potassium carbonate (0.88 g) and TDA-1 (0.27 g) in acetonitrile (10 g) was refluxed for 5 hours. After cooling, the reaction mixture was diluted with 3% hydrochloric acid (200 ml) and extracted with ethyl acetate. The organic layer was washed with 5% sodium carbonate solution, water and saturate sodium chloride solution in order, dried over magnesium sulfate, filtered and concentrated. The precipitated crystals were collected by filtration and recrystallized from methanol to give ethyl 2,4-dinitro-5-chlorophenoxyacetate (1.9 g; yield, 73.9%). M.P., 129°-130° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 5% sodium carbonate solution, water
  4. concentrationsaturate sodium chloride solution in order
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationThe precipitated crystals were collected by filtration
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-78da6eda1e2543d0862526d457f1f74e
Source dataset
uspto-grants-1989_02
Patent number
US04803270

Reaction notes

Loading…