Butanal → 5-Oxooctanenitrile

HRID 258946Notes

Reaction equation

[CH:1](=[O:5])[CH2:2][CH2:3][CH3:4].[CH2:6]([N:8](CC)CC)C.[C:13](#N)[CH:14]=[CH2:15]>CN(C)C=O>[O:5]=[C:1]([CH2:13][CH2:14][CH3:15])[CH2:2][CH2:3][CH2:4][C:6]#[N:8]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 36 g (1.0 mol) of distilled n-butyraldehyde, 13.5 g (0.05 mol) of Catalyst 1, 400 ml of dimethylformamide and 20.2 g (0.2 mol) of triethylamine is initially introduced, under nitrogen, into the apparatus described in Example 1. The mixture is stirred for 2 hours at 80° C and a solution of 26.5 g (0.5 mol) of distilled acrylonitrile is then added dropwise over the course of 6 hours. The whole is then stirred for a further 16 hours at the same temperature. For working up, the solvent is distilled off in vacuo, the oil which remains is taken up in chloroform and the solution is washed with water, dilute sodium bisulphite solution and again with water. The organic layer is separated off and dried with magnesium sulphate. It is filtered, solvent is distilled off and the residue is distilled in a water-pump vacuum. 4-Oxo-heptane-1-carbonitrile is obtained.

Workup

additionis initially introduced, under nitrogen, into the apparatus
stirringThe whole is then stirred for a further 16 hours at the same temperature
distillationthe solvent is distilled off in vacuo
washthe solution is washed with water, dilute sodium bisulphite solution and again with water
customThe organic layer is separated off
dry with materialdried with magnesium sulphate
filtrationIt is filtered
distillationsolvent is distilled off
distillationthe residue is distilled in a water-pump vacuum

Sources & evidence

ORD record: ord-0dd7d0cd9581432a9a2a36fcbd4ff204
Source dataset: uspto-grants-1977_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04035395

Reaction notes

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