4-Nitrobenzaldehyde → HCID 23912199, compound

HRID 1088189Notes

Reaction equation

HRID 1088189 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[OH-].[Na+].[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)([O-:16])=[O:15]>C1(C)C=CC=CC=1.O>[C:10]([C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[CH:21][C:20]1[CH:23]=[CH:24][C:17]([N+:14]([O-:16])=[O:15])=[CH:18][CH:19]=1)#[N:11]

Participants

6

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 14798Sodium HydroxideHCID 66031Benzeneacetonitrile, 4-methoxy-

Product 1

HCID 23912199HCID 23912199, compoundYield 6.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
20 °C

Procedure

4-Methoxyphenylacetonitrile (7.63 g, 50 mmol) in toluene (30 mL), PEG(E)-400 (4 g, 10 mmol) and 52% aqueous sodium hydroxide (10.73 g in 12.4 mL water) were placed in a flask equipped with a magnetic stirrer. 4-Nitrobenzaldehyde (7.56 g, 50 mmol) in a minimum of toluene was added dropwise. The mixture was stirred for 1 h at 20° C. and then diluted with water (30 mL). The organic layer was separated, washed with water (3×40 mL) and dried with sodium sulfate. The solvent was removed under reduced pressure and the residue was recrystallized from toluene at -20° C. to give 1-cyano-1-(4-methoxyphenyl)-2-(4-nitrophenyl)ethylene (yield=0.913 g, 6.5%).

Workup

  1. customequipped with a magnetic stirrer
  2. customThe organic layer was separated
  3. washwashed with water (3×40 mL)
  4. dry with materialdried with sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was recrystallized from toluene at -20° C.

Sources & evidence

ORD record
ord-f6e1151de07b4f1a86ee28cd780689e3
Source dataset
uspto-grants-1990_10
Patent number
US04961631

Reaction notes

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