Sodium amide → 5,5-Diethoxy-2-isopropyl-2-(2-methylphenyl) valeronitrile

HRID 231655

Reaktionsgleichung

Reaktionsgleichung von HRID 231655
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH:11]([CH3:13])[CH3:12])[C:9]#[N:10].[CH2:14]([O:16][CH:17]([O:21][CH2:22][CH3:23])[CH2:18][CH2:19]Cl)[CH3:15].[H-].[Na+].[NH2-].[Na+]>C1(C)C=CC=CC=1.COCCOC.CN(C)C=O.C1(C)C(C)=CC=CC=1.C1C=CC=CC=1>[CH2:14]([O:16][CH:17]([O:21][CH2:22][CH3:23])[CH2:18][CH2:19][C:8]([CH:11]([CH3:13])[CH3:12])([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])[C:9]#[N:10])[CH3:15]

Komponenten

10

Edukt 4

HCID 24533Sodium amide2×HCID 24758Sodium hydrideHCID 962173-Chloro-1,1-diethoxypropaneHCID 142451303-Methyl-2-(2-methylphenyl)butanenitrile

Produkt 1

HCID 142451405,5-Diethoxy-2-isopropyl-2-(2-methylphenyl) valeronitrile

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 241BenzeneLösungsmittelHCID 1140TolueneLösungsmittel2×HCID 6228DimethylformamideLösungsmittelHCID 7237O-XyleneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

The alkylation of 2-(2-methylphenyl)-3-methylbutyronitrile of Formula II: ##STR3## with 3,3-diethoxypropylchloride is carried out conveniently in an inert organic solvent in the presence of an alkaline condensing agent. Suitable inert organic solvents are aromatic hydrocarbons, e.g. benzene, toluene or commercial xylene, tertiary amides, e.g. dimethylformamide, or higher-boiling aliphatic ethers, e.g. ethyleneglycol dimethylether. Preferable alkaline condensing agent is sodium hydride or sodium amide. The reaction is advantageously effected by dropping a toluenic sodium amide suspension to a boiling solution of the above reactants in anhydrous toluene and refluxing the mixture for a period of 4 to 10 hours. The so formed acetal, 5,5-diethoxy-2-isopropyl-2-(2-methylphenyl) valeronitrile of Formula III: ##STR4## is isolated on cooling the mixture by short agitation with water, separation of the toluenic phase and evaporation of the solvent. The obtained crude product is purified by distillation under reduced pressure.

Aufarbeitung

  1. customPreferable alkaline condensing agent
  2. temperaturerefluxing the mixture for a period of 4 to 10 hours

Quellen und Nachweise

ORD-Eintrag
ord-0e189ea67b774e1c8e29061ef379abed
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04847403

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