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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 231655Generated: October 26, 2026

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

https://huagongshe.com/reaction/231655

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium amideHCID 24533—
ReactantSodium hydrideHCID 24758—
Reactant3-Chloro-1,1-diethoxypropaneHCID 96217—
Reactant3-Methyl-2-(2-methylphenyl)butanenitrileHCID 14245130—
SolventBenzeneHCID 241—
SolventTolueneHCID 1140—
SolventDimethylformamideHCID 6228—
SolventO-XyleneHCID 7237—
Solvent1,2-DimethoxyethaneHCID 8071—
Product5,5-Diethoxy-2-isopropyl-2-(2-methylphenyl) valeronitrileHCID 14245140—

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04847403
Source datasetuspto-grants-1989_07
ORD IDord-0e189ea67b774e1c8e29061ef379abed
Source noteuspto-grants-1989_07