Hydrochloric Acid → 3-(3-Formyl-4-nitrophenoxy)-benzonitrile

HRID 1968791Notes

Reaction equation

HRID 1968791 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12].Cl.C1COCC1>O>[CH:3]([C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 586250533-(3-Dimethoxymethyl-4-nitrophenoxy)-benzonitrile

Product 1

HCID 586250423-(3-Formyl-4-nitrophenoxy)-benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3-(3-dimethoxymethyl-4-nitro-phenoxy)-benzonitrile (0.068 mol) in water (55 mL) was stirred at room temperature, and then 12N HCl (55 mL) and THF (140 mL) were added, and the reaction mixture was stirred overnight at room temperature. The mixture was stirred in H2O and extracted with diisopropyl ether. The organic layer was separated, washed with a 10% NaHCO3 solution, separated again, dried, filtered off and the solvent was evaporated. The obtained residue was stirred in diisopropyl ether, and then the desired product was filtered off and dried to yield the title compound as a solid.

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. extractionextracted with diisopropyl ether
  3. customThe organic layer was separated
  4. washwashed with a 10% NaHCO3 solution
  5. customseparated again
  6. customdried
  7. filtrationfiltered off
  8. customthe solvent was evaporated
  9. stirringThe obtained residue was stirred in diisopropyl ether
  10. filtrationthe desired product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-705736079a974796b8a70784c6ddf67f
Source dataset
uspto-grants-2013_04
Patent number
US08426429B2

Reaction notes

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