Benzene → 1-Nitro-2-(1,3-pentadienyl)benzene

HRID 374001Notes

Reaction equation

HRID 374001 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[CH:6]=[CH:7][CH:8]=O)([O-:3])=[O:2].[OH-].[Na+].[CH:16]1C=CC=C[CH:17]=1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[CH:6]=[CH:7][CH:8]=[CH:16][CH3:17])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 241BenzeneHCID 14798Sodium HydroxideHCID 73842CID 73842

Product 1

HCID 541557381-Nitro-2-(1,3-pentadienyl)benzeneYield 98%

Reagents, catalysts & solvents 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Catalyst

Procedure

10 g of o-nitrocinnamaldehyde was dissolved in 150 ml of benzene. Thereto were added 25 g of ethyltriphenylphosphonium bromide and 150 ml of a 5 N aqueous sodium hydroxide solution. The mixture was stirred at room temperature for 2 hours. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distil-lation under reduced pressure. The residue was purified by column chromatography (eluant: toluene) to obtain 10.4 g (yield: 98%) of 1-nitro-2-(1,3-pentadienyl)-benzene as a light yellow oily material.

Workup

  1. customThe organic layer was separated
  2. washwashed with an aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed
  5. customby distil-lation under reduced pressure
  6. customThe residue was purified by column chromatography (eluant: toluene)

Sources & evidence

ORD record
ord-35ebe2b7fdc94b859a9aac06a46ce2ac
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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