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

HRID 374003

Reaktionsgleichung

Reaktionsgleichung von HRID 374003
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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-43144c0ad6ff45aba5b735de56d1b6f5
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166204

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