Hydroquinone → HCID 57110748, compound

HRID 1706641Notes

Reaction equation

HRID 1706641 reaction equation
[C:1]1([OH:8])[CH:6]=[CH:5][C:4]([OH:7])=[CH:3][CH:2]=1.[OH2:9].[OH-:10].[K+].Cl[C:13]1[CH:14]=[CH:15][C:16]([N+:21]([O-:23])=[O:22])=[C:17]([CH:20]=1)[C:18]#[N:19]>CC(N(C)C)=O.C1(C)C=CC=CC=1>[N+:21]([C:16]1[CH:15]=[CH:14][C:13]([O:7][C:4]2[CH:5]=[CH:6][C:1]([O:8][C:13]3[CH:14]=[CH:15][C:16]([N+:21]([O-:10])=[O:9])=[C:17]([C:18]#[N:19])[CH:20]=3)=[CH:2][CH:3]=2)=[CH:20][C:17]=1[C:18]#[N:19])([O-:23])=[O:22]

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 962Water2×HCID 14797Potassium HydroxideHCID 1005065-Chloro-2-nitrobenzonitrile

Product 1

HCID 57110748HCID 57110748, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 5.51 g. (0.05 mole) of 1,4 benzenediol in 100 ml. of water was stirred under nitrogen while a solution of 6.47 g. (0.10 mole) of potassium hydroxide (86.5%) in 20 ml. of water was added, followed by 200 ml. of toluene. The mixture was refluxed with stirring, using a Dean-Stark trap, until the water was largely removed. Dimethylacetamide (200 ml.) was then added, and solvent was distilled off until the pot temperature reached 150° C. The mixture was cooled to 50° C., and a solution of 18.26 g. (0.10 mole) of 5-chloro-2-nitro-benzonitrile (Aldrich Chemical Co.) in 50 ml. of dimethylacetamide was added with stirring. The mixture was stirred for 90 minutes at room temperature, 2 hrs. at 125° C., and 1 hr. at 155° C. After cooling to room temperature it was filtered. The filtrate was evaporated to dryness and the residue washed with 250 ml. of tetrahydrofuran. The residual solid was dried in vacuum at 100° C. to give 11.64 g. (58% yield) of hydroquinone bis(4-nitro-3-cyanophenyl) ether, m.p. 233° C. Anal: Calculated for C20H10N4O6 : C, 59.71; H, 2.51; N, 13.92; O, 23.86. Found: C, 59.27, 59.42; H, 2.85, 2.75; N, 13.81, 13.60; O, 24.18, 23.92. An additional 1.48 g. (7.4% yield) of product was recovered from the tetrahydrofuran washings.

Workup

  1. temperatureThe mixture was refluxed
  2. customuntil the water was largely removed
  3. additionDimethylacetamide (200 ml.) was then added
  4. distillationsolvent was distilled off until the pot temperature
  5. customreached 150° C
  6. stirringwith stirring
  7. stirringThe mixture was stirred for 90 minutes at room temperature, 2 hrs
  8. customat 125° C.
  9. custom1 hr
  10. customat 155° C
  11. temperatureAfter cooling to room temperature it
  12. filtrationwas filtered
  13. customThe filtrate was evaporated to dryness
  14. washthe residue washed with 250 ml
  15. customThe residual solid was dried in vacuum at 100° C.
  16. customto give 11.64 g

Sources & evidence

ORD record
ord-1f336c0b64f24c9881f90ce5fb903117
Source dataset
uspto-grants-1980_06
Patent number
US04208343

Reaction notes

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