Pent-2-enenitrile → Methyl formate

HRID 2416180Notes

Reaction equation

HRID 2416180 reaction equation
COC[C:4]([O:9][CH3:10])([O:7][CH3:8])[O:5][CH3:6].C(#N)C=CCC>>[CH:4]([O:9][CH3:10])([O:7][CH3:8])[O:5][CH3:6].[CH:4]([O:5][CH3:6])=[O:7].[CH3:6][O:5][CH2:4][O:7][CH3:8]

Participants

5

Reactant 2

HCID 25833Pent-2-enenitrileHCID 1418971,1,1,2-Tetramethoxyethane

Product 3

HCID 7865Methyl formateHCID 8020DimethoxymethaneHCID 9005Trimethyl orthoformate

Procedure

The electrolysis was discontinued after 10 h, when 64% of tetramethoxyethane and 76% of pentenenitrile had been converted. Trimethyl orthoformate, methyl formate and formaldehyde dimethyl acetal had formed at the anode in a ratio of 1:0.17:0.1. The main products at the cathode were 3.4-diethyladiponitrile, pentanenitrile and 3-methoxypentanenitrile in a ratio of 1:0.3:0.8. A distillative workup provided the hydrodimerization 20 product of pentenenitrile, namely 3.4-diethyladiponitrile, in 97% purity.

Sources & evidence

ORD record
ord-4d7e4851ed6c4c7e922d1c5d8d6d800e
Source dataset
uspto-grants-2004_11
Patent number
US06822124B2

Reaction notes

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