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

HRID 390273Notes

Reaction equation

HRID 390273 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 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(3-dimethoxymethyl-4-nitro-phenoxy)-benzonitrile (0.068 mol) in THF (140 ml) was stirred at room temperature, then 12N HCl (55 ml) and water (55 ml) were added and the reaction mixture was stirred overnight at room temperature. The mixture was stirred in H2O and extracted with DIPE. 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 DIPE, then the desired product was filtered off and dried to yield the title compound as a residue.

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. extractionextracted with DIPE
  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 DIPE
  10. filtrationthe desired product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-7c7588e400864886a26cfdc4ff9b399d
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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