Methacrolein → 1-(3-Methyl-1,3-butadienyl)-2-nitrobenzene

HRID 374003Notes

Reaction equation

HRID 374003 reaction equation
O=[CH:2][C:3](=[CH2:5])[CH3:4].[Br-].[N+:7]([C:10]1[CH:35]=[CH:34][CH:33]=[CH:32][C:11]=1[CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O-:9])=[O:8].[OH-].[Na+]>C1C=CC=CC=1>[CH3:4][C:3](=[CH2:5])[CH:2]=[CH:12][C:11]1[CH:32]=[CH:33][CH:34]=[CH:35][C:10]=1[N+:7]([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 6562MethacroleinHCID 14798Sodium HydroxideHCID 10885283(2-Nitrobenzyl)triphenylphosphonium bromide

Product 1

HCID 537916531-(3-Methyl-1,3-butadienyl)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5.0 ml of methacrolein was dissolved in 100 ml of benzene. Thereto were added 31.5 g of 2-nitro-benzyltriphenylphosphonium bromide and 100 ml of a 5 N aqueous sodium hydroxide solution. The mixture was stirred at room temperature for 5 hours. The organic layer was separated and washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene) to obtain 2.7 g of 1-(3-methyl-1,3-butadienyl)-2-nitrobenzene (containing about 2.2 g of o-nitrotoluene) 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 by distillation under reduced pressure
  5. customThe residue was purified by column chromatography (eluant: toluene)

Sources & evidence

ORD record
ord-43144c0ad6ff45aba5b735de56d1b6f5
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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