Hydroxyacetonitrile → (5-Chloro-2,4-dinitrophenoxy)acetonitrile

HRID 1381632Notes

Reaction equation

HRID 1381632 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](#[N:18])[CH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[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]#[N:18])([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 7857HydroxyacetonitrileHCID 11430Potassium CarbonateHCID 772861,3-Dichloro-4,6-dinitrobenzene

Product 1

HCID 14250577(5-Chloro-2,4-dinitrophenoxy)acetonitrileYield 58.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1,5-dichloro-2,4-dinitrobenzene (5.0 g), glycolonitrile (1.81 g) and anhydrous potassium carbonate (2.19 g) in dimethylformamide (20 g) was stirred at 25° to 30° C. for 24 hours. After completion of the reaction, the reaction mixture was diluted with water (200 ml) and extracted with ethyl acetate (200 ml). The organic layer was washed with water, dried over magnesium sulfate and concentrated. The precipitated crystals were collected by filtration and washed with ether to give crude crystals (4.16 g), which were recrystallized from methanol to give 2,4-dinitro-5-chlorophenoxyacetonitrile (3.18 g; yield, 58.5%). M.P., 117°-118° C.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (200 ml)
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with ether
  8. customto give crude crystals (4.16 g), which
  9. customwere recrystallized from methanol

Sources & evidence

ORD record
ord-3f6feeaeb50946e1b43b67629668cfd6
Source dataset
uspto-grants-1989_02
Patent number
US04803270

Reaction notes

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