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
Participants
| Role | Name | HCID | Charge |
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| Reactant | Sodium amide | HCID 24533 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 3-Chloro-1,1-diethoxypropane | HCID 96217 | — |
| Reactant | 3-Methyl-2-(2-methylphenyl)butanenitrile | HCID 14245130 | — |
| Solvent | Benzene | HCID 241 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 5,5-Diethoxy-2-isopropyl-2-(2-methylphenyl) valeronitrile | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04847403 |
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| Source dataset | uspto-grants-1989_07 |
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| ORD ID | ord-0e189ea67b774e1c8e29061ef379abed |
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| Source note | uspto-grants-1989_07 |
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