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molecular formula C6H9NO B8775220 4-Methyl-5-oxopentanenitrile

4-Methyl-5-oxopentanenitrile

Cat. No. B8775220
M. Wt: 111.14 g/mol
InChI Key: WZGRZLPEJDJMAI-UHFFFAOYSA-N
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Patent
US04102913

Procedure details

In the presence of alkaline catalysts, acrylonitrile reacts with aldehydes, the α-carbon atoms of which possess one or two hydrogen atoms, forming 3-substituted propionitriles (U.S. Pat. No. 2,353,687). This so-called "cyanoethylation" reaction also occurs with other compounds which have an active hydrogen atom. For example, 2-ethyl butyraldehyde and acrylonitrile react in the presence of catalytic amounts of 50 percent caustic potash solution forming 2-(β-cyanoethyl)-2-ethyl butyraldehyde. A yield of 76.6 percent results after a reaction period of 4.5 hours. (H. A. Bruson, Th. W. Riener, J. Am. Chem. Soc., 66, 57 [1944]). The reaction is strongly exothermal. Acetaldehyde reacts with acrylonitrile in the presence of a 50 percent caustic soda solution forming γ-formylpimelonitrile. For a yield of 40-50%, the reaction period amounts to 2-3 hours. Under the same conditions, propionaldehyde forms 4.9 percent 2-methyl-4-cyanobutyraldehyde (U.S. Pat. No. 2,409,086). 2,2-dimethyl-4-cyano-butyraldehyde is formed in up to 60 percent yield from the reaction between isobutyraldehyde and acrylonitrile.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two

Identifiers

REACTION_CXSMILES
[CH:1](=[O:4])[CH2:2][CH3:3].[CH3:5][CH:6]([CH2:9][CH2:10][C:11]#[N:12])[CH:7]=[O:8]>>[CH3:5][C:6]([CH3:1])([CH2:9][CH2:10][C:11]#[N:12])[CH:7]=[O:8].[CH:1](=[O:4])[CH:2]([CH3:5])[CH3:3].[C:1](#[N:12])[CH:2]=[CH2:3]

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(CC)=O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C=O)CCC#N

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
For a yield of 40-50%, the reaction period

Outcomes

Product
Details
Reaction Time
2.5 (± 0.5) h
Name
Type
product
Smiles
CC(C=O)(CCC#N)C
Name
Type
product
Smiles
C(C(C)C)=O
Name
Type
product
Smiles
C(C=C)#N

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US04102913

Procedure details

In the presence of alkaline catalysts, acrylonitrile reacts with aldehydes, the α-carbon atoms of which possess one or two hydrogen atoms, forming 3-substituted propionitriles (U.S. Pat. No. 2,353,687). This so-called "cyanoethylation" reaction also occurs with other compounds which have an active hydrogen atom. For example, 2-ethyl butyraldehyde and acrylonitrile react in the presence of catalytic amounts of 50 percent caustic potash solution forming 2-(β-cyanoethyl)-2-ethyl butyraldehyde. A yield of 76.6 percent results after a reaction period of 4.5 hours. (H. A. Bruson, Th. W. Riener, J. Am. Chem. Soc., 66, 57 [1944]). The reaction is strongly exothermal. Acetaldehyde reacts with acrylonitrile in the presence of a 50 percent caustic soda solution forming γ-formylpimelonitrile. For a yield of 40-50%, the reaction period amounts to 2-3 hours. Under the same conditions, propionaldehyde forms 4.9 percent 2-methyl-4-cyanobutyraldehyde (U.S. Pat. No. 2,409,086). 2,2-dimethyl-4-cyano-butyraldehyde is formed in up to 60 percent yield from the reaction between isobutyraldehyde and acrylonitrile.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two

Identifiers

REACTION_CXSMILES
[CH:1](=[O:4])[CH2:2][CH3:3].[CH3:5][CH:6]([CH2:9][CH2:10][C:11]#[N:12])[CH:7]=[O:8]>>[CH3:5][C:6]([CH3:1])([CH2:9][CH2:10][C:11]#[N:12])[CH:7]=[O:8].[CH:1](=[O:4])[CH:2]([CH3:5])[CH3:3].[C:1](#[N:12])[CH:2]=[CH2:3]

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(CC)=O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CC(C=O)CCC#N

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
For a yield of 40-50%, the reaction period

Outcomes

Product
Details
Reaction Time
2.5 (± 0.5) h
Name
Type
product
Smiles
CC(C=O)(CCC#N)C
Name
Type
product
Smiles
C(C(C)C)=O
Name
Type
product
Smiles
C(C=C)#N

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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