Hydroxymethylene Ketones. IV. Orientation in the Condensation of Methyl n-Hexyl Ketone with Methyl Formate

Royals, E. Earl; Covington, Elzbieta

doi:10.1021/ja01616a084

Cited by 9 publications

(2 citation statements)

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“…The lines were fitted by the method of least squares. The vapor pressure equations for the two acids were established graphically and are found to be 2-Ethyiheptanoic: log P,:mnli = ~^14 + 9.28 (386.66 g T g 474.66) (Standard deviation: 1.28 mm. Hg) Pelargonic: log P:mm = + 9.23 (386.66 g T g 483.16) (Standard deviation: 2.66 mm.…”

Section: Resultsmentioning

confidence: 99%

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Some Physical Properties of Certain C₉ and C₁₀ Aliphatic Acids and their Methyl Esters.2-Ethylheptanoic and Pelargonic Acids, and Methyl Esters of 2-Ethylpentanoic,Pelargonic, 2, 5-Diethyladipic, 2-Ethylsuberic, and Sebacic Acids.

Trent¹,

Miller²,

Brown³

1960

J. Chem. Eng. Data

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Section: Resultsmentioning

confidence: 99%

“…Royals and Covington (9) describe the preparation of 2-ethylheptanoic acid and give its boiling point as 121-2°C . (6 mm.…”

mentioning

confidence: 99%

Some Physical Properties of Certain C₉ and C₁₀ Aliphatic Acids and their Methyl Esters.2-Ethylheptanoic and Pelargonic Acids, and Methyl Esters of 2-Ethylpentanoic,Pelargonic, 2, 5-Diethyladipic, 2-Ethylsuberic, and Sebacic Acids.

Trent¹,

Miller²,

Brown³

1960

J. Chem. Eng. Data

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The γ‐Alkylation and γ‐Arylation of Dianions of β‐Dicarbonyl Compounds

Harris

2011

Organic Reactions

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It is well known that beta‐diketones can undergo condensations at the alpha‐methylene group with alkyl halides and certain other reagents though the intermediate formation of monoanions. For example, acetylacetone on treatment with an alkali metal or an alkali metal alkoxide or carbonate forms a mono‐anion which can be alkylated with alkyl halides. In 1958, Hauser and Harris reported that, if benzoylacetone or acetylacetone is first converted to the dipotassium salt. The salt undergoes alkylation and other carbon‐carbon condensations at the terminal methyl group rather than at the methylene group. Rapid alkylation was observed when the salts were treated with benzyl chloride and after acidification, the terminal monobenzylation derivatives were obtained in good yield. Dibenzylation was not observed. In this chapter alkylations of these and other beta‐ketones via dianions are surveyed. Other alkylations are also discussed. Arylations are included because alkylation and arylation are methods for directly converting beta‐homologs without increasing their functionality.

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Bénary Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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The reaction between a Grignard reagent (or an organolithium reagent) and an enamino ketone or aldehyde to yield an αβ‐unsaturated ketone or aldehyde and αβ‐unsaturated esters with stereoselectivity, is generally known as the Bénary reaction. This reaction has been reported to follow the different mechanisms—for example, in the case of β‐amino vinyl ketones, the reaction seems to proceed through a 1,4‐addition‐elimination, whereas β‐aminopropenals seems to react with organomagnesium and organolithium reagents mainly via a 1,2‐addition at the carbonyl group. High yields in the reaction have been observed when the reactions are carried out in toluene with Grignard reagents.

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Hydroxymethylene Ketones. IV. Orientation in the Condensation of Methyl n-Hexyl Ketone with Methyl Formate

Cited by 9 publications

References 1 publication

Some Physical Properties of Certain C₉ and C₁₀ Aliphatic Acids and their Methyl Esters.2-Ethylheptanoic and Pelargonic Acids, and Methyl Esters of 2-Ethylpentanoic,Pelargonic, 2, 5-Diethyladipic, 2-Ethylsuberic, and Sebacic Acids.

Some Physical Properties of Certain C₉ and C₁₀ Aliphatic Acids and their Methyl Esters.2-Ethylheptanoic and Pelargonic Acids, and Methyl Esters of 2-Ethylpentanoic,Pelargonic, 2, 5-Diethyladipic, 2-Ethylsuberic, and Sebacic Acids.

The γ‐Alkylation and γ‐Arylation of Dianions of β‐Dicarbonyl Compounds

Bénary Reaction

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Hydroxymethylene Ketones. IV. Orientation in the Condensation of Methyl n-Hexyl Ketone with Methyl Formate

Cited by 9 publications

References 1 publication

Some Physical Properties of Certain C9 and C10 Aliphatic Acids and their Methyl Esters.2-Ethylheptanoic and Pelargonic Acids, and Methyl Esters of 2-Ethylpentanoic,Pelargonic, 2, 5-Diethyladipic, 2-Ethylsuberic, and Sebacic Acids.

Some Physical Properties of Certain C9 and C10 Aliphatic Acids and their Methyl Esters.2-Ethylheptanoic and Pelargonic Acids, and Methyl Esters of 2-Ethylpentanoic,Pelargonic, 2, 5-Diethyladipic, 2-Ethylsuberic, and Sebacic Acids.

The γ‐Alkylation and γ‐Arylation of Dianions of β‐Dicarbonyl Compounds

Bénary Reaction

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Some Physical Properties of Certain C₉ and C₁₀ Aliphatic Acids and their Methyl Esters.2-Ethylheptanoic and Pelargonic Acids, and Methyl Esters of 2-Ethylpentanoic,Pelargonic, 2, 5-Diethyladipic, 2-Ethylsuberic, and Sebacic Acids.

Some Physical Properties of Certain C₉ and C₁₀ Aliphatic Acids and their Methyl Esters.2-Ethylheptanoic and Pelargonic Acids, and Methyl Esters of 2-Ethylpentanoic,Pelargonic, 2, 5-Diethyladipic, 2-Ethylsuberic, and Sebacic Acids.