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

HRID 231655

反応式

HRID 231655 の反応式
[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]

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 241Benzene溶媒HCID 1140Toluene溶媒2 回HCID 6228Dimethylformamide溶媒HCID 7237O-Xylene溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-0e189ea67b774e1c8e29061ef379abed
出典データセット
uspto-grants-1989_07
特許番号
US04847403

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