The Condensation of 2-Butanone with Aldehydes of the Type RR'CHCHO<sup>1,2</sup>

Powell, S. G.; Baldwin, M. M.

doi:10.1021/ja01301a013

Cited by 14 publications

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“…4-Ethyloctanoic acid can be synthesized by several methods. One method is that of S. G. Powell’s from 2-ethyl-1-bromohexane and diethyl malonate [ 11 ] ( Scheme 1 ). This method offers the advantage of cheap and available materials with mild reaction conditions, but requires long reaction times [ 12 – 15 ].…”

Section: Introductionmentioning

confidence: 99%

Rapid Synthesis of Flavor Compound 4-Ethyloctanoic Acid under Microwave Irradiation

Liu

Yin

Chen

et al. 2010

IJMS

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Rapid synthesis of 4-ethyloctanoic acid by means of microwave irradiation is described. Diethyl malonate reacted with 2-ethyl-1-bromohexane in the presence of sodium ethoxide to give diethyl (2-ethylhexyl)malonate (1b). 1b was saponified in the solution of ethanol and potassium hydroxide and then acidified to form (2-ethylhexyl)propanedioic acid (1c), and 1c was heated and decarboxylized to give 4-ethyloctanoic acid (1d). The influence of reaction temperature and reaction time on the yield of 1b and the effect of reaction time on the yield of 1c and 1d were investigated in order to optimize the synthetic conditions. The relative optimal conditions for the synthesis of 1b were a mole ratio of sodium to diethyl malonate to 2-ethylhexyl bromide of 0.1:0.11:0.11, a reaction temperature of 80–85 °C, and a reaction time of 2–2.5 h. The yield of 1b was about 79%. 1b was saponified for 30 min and then acidified to form 1c, and the yield of 1c was 96%. 1c was heated for 16 min at 180°C to give 1d, and the yield of 1d was about 90%. The overall yield of 1d is 70% under microwave irradiation. The reaction time was reduced greatly. In order to compare the result of microwave irradiation with that of an oil bath, the reactions were also performed in an oil bath. The structures of intermediates, product and by-product were confirmed by HRMS, 1H NMR, 13C-NMR and IR.

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Section: Introductionmentioning

confidence: 99%

Rapid Synthesis of Flavor Compound 4-Ethyloctanoic Acid under Microwave Irradiation

Liu

Yin

Chen

et al. 2010

IJMS

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“…The identity of this product was demonstrated by its hydrogenation over platinum to ethyl 2-cyano-4-ethyloctanoate and hydrolysis of this cyanoester to 4-ethyloctanoic acid (13). The cyanoacetate and acid were also prepared when either 2-ethylhexanal or 2-ethyl-2-hexenal was initially condensed with ethyl cyanoacetate, hydrogenated and hydrolyzed, Table V.…”

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confidence: 96%

Catalyst Study of the Knoevenagel Condensation.

Prout¹,

Abdel‐Latif²,

Kamal³

1963

J. Chem. Eng. Data

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“…Analysis of this salt showed that a 6-carbon atom acid (isocaproic acid) had been formed by reduction of the pyrone, whereas, if methylation on carbon atom 6 had occurred, a 7-carbon atom acid (7-methylcaproic acid) would have been formed. The piperazonium salt of the latter is reported as melting at 109° ( 9).…”

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confidence: 99%

STUDIES ON LACTONES RELATED TO THE CARDIAC AGLYCONES. VI. THE ACTION OF DIAZOMETHANE ON CERTAIN DERIVATIVES OF Α-Pyrone

Fried¹,

Elderfield²

1941

J. Org. Chem.

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The Condensation of 2-Butanone with Aldehydes of the Type RR'CHCHO^1,2

Cited by 14 publications

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Rapid Synthesis of Flavor Compound 4-Ethyloctanoic Acid under Microwave Irradiation

Rapid Synthesis of Flavor Compound 4-Ethyloctanoic Acid under Microwave Irradiation

Catalyst Study of the Knoevenagel Condensation.

STUDIES ON LACTONES RELATED TO THE CARDIAC AGLYCONES. VI. THE ACTION OF DIAZOMETHANE ON CERTAIN DERIVATIVES OF Α-Pyrone

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The Condensation of 2-Butanone with Aldehydes of the Type RR'CHCHO1,2

Cited by 14 publications

References 0 publications

Rapid Synthesis of Flavor Compound 4-Ethyloctanoic Acid under Microwave Irradiation

Rapid Synthesis of Flavor Compound 4-Ethyloctanoic Acid under Microwave Irradiation

Catalyst Study of the Knoevenagel Condensation.

STUDIES ON LACTONES RELATED TO THE CARDIAC AGLYCONES. VI. THE ACTION OF DIAZOMETHANE ON CERTAIN DERIVATIVES OF Α-Pyrone

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The Condensation of 2-Butanone with Aldehydes of the Type RR'CHCHO^1,2