Hydrochloric Acid → 4,6-Dinitroresorcinol

HRID 2211334

Reaction equation

HRID 2211334 reaction equation
C[O:2][C:3]1[C:4]([N+:13]([O-:15])=[O:14])=[CH:5][C:6]([N+:10]([O-:12])=[O:11])=[C:7]([OH:9])[CH:8]=1.CN(C)C=O.Cl.Cl>CN(C)C=O>[N+:10]([C:6]1[CH:5]=[C:4]([N+:13]([O-:15])=[O:14])[C:3]([OH:2])=[CH:8][C:7]=1[OH:9])([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2667955-Methoxy-2,4-dinitrophenol2×HCID 10920465N,N-dimethylformamide;hydrochloride

Product 1

HCID 611584,6-DinitroresorcinolYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a 100 mL round-bottom flask is added 2.14 g (10 mmol) of 5-methoxy-2,4-dinitrophenol (MDNP) and 1.31 g (12 mmol) of DMF-HCl in 30 mL of N,N-dimethylformamide (DMF). This mixture is stirred at 130° C. and monitored by High Pressure Liquid Chromatography (HPLC). After 8.5 hours essentially no MDNP is observed by HPLC. The reaction mixture is poured into 100 mL of 1N HCl, and extracted with ethyl acetate (EtOAc, 3×30 mL). The combined organics are washed with a single portion of 0.1N HCl, dried (Na2SO4) and concentrated by rotary evaporation to give crude 4,6-dinitroresorcinol (DNR) as a yellow solid (1.9 g, 95% yield): melting point (m.p.) 205° C. to 210° C., 1H NMR (CDCl3)δ11.03 (s,2H), 9.08 (s,1H), 6.82 (s,1H).

Workup

  1. extractionextracted with ethyl acetate (EtOAc, 3×30 mL)
  2. washThe combined organics are washed with a single portion of 0.1N HCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-764ba658150c4f60b7e970e197d8ecff
Source dataset
uspto-grants-1995_10
Patent number
US05463129

Linked notes

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