Benzyl Chloride → 1-Nitro-2-(2-phenylethenyl)benzene

HRID 1282871Notes

Reaction equation

HRID 1282871 reaction equation
C1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Na].[N+:29]([C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH:34]=O)([O-:31])=[O:30]>C(O)C>[N+:29]([C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH:34]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([O-:31])=[O:30]

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 111012-NitrobenzaldehydeHCID 5241824TriphenylphosphoniumHCID 5360545Sodium

Product 1

HCID 199081-Nitro-2-(2-phenylethenyl)benzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The triphenylphosphonium salt of benzyl chloride (38.9 g., 0.10 mole) is added to a solution of sodium (3.0 g.) in ethanol (200 ml.). The resulting solution is treated with 2-nitrobenzaldehyde (16 g., 0.10 mole) and stirred overnight. The mixture is filtered, washed with water and extracted with dichloromethane. The extracts are evaporated to a dark residue which is extracted with carbon tetrachloride, then these extracts are concentrated and passed through a column of alumina, eluting with hexane and carbon tetrachloride to give a yellow oil, 2-nitrostilbene.

Workup

  1. filtrationThe mixture is filtered
  2. washwashed with water
  3. extractionextracted with dichloromethane
  4. customThe extracts are evaporated to a dark residue which
  5. extractionis extracted with carbon tetrachloride
  6. concentrationthese extracts are concentrated
  7. washeluting with hexane and carbon tetrachloride

Sources & evidence

ORD record
ord-e1d3da16a6db4968957afb5bb7f90a78
Source dataset
uspto-grants-1976_08
Patent number
US03972926

Reaction notes

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