The Preparation of Cyclopentenones from Lactones

Frank, Robert; Armstrong, Rose; Kwiatek, Jack; Price, Harold A.

doi:10.1021/ja01184a026

Cited by 23 publications

(13 citation statements)

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“…The 'H n.m.r. spectra of these products were very similar, with 2 H peaks at 6 6.46 (12) and 6.44 (13), characteristic of a hydrogen atom on a carbon adjacent to an oxygen atom,' and a…”

Section: Resultsmentioning

confidence: 92%

Reactions of some cyclic ethers in superacids

Baig¹,

Banthorpe²,

Carr³

et al. 1989

J. Chem. Soc., Perkin Trans. 2

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“…The 'H n.m.r. spectra of these products were very similar, with 2 H peaks at 6 6.46 (12) and 6.44 (13), characteristic of a hydrogen atom on a carbon adjacent to an oxygen atom,' and a…”

Section: Resultsmentioning

confidence: 92%

Reactions of some cyclic ethers in superacids

Baig¹,

Banthorpe²,

Carr³

et al. 1989

J. Chem. Soc., Perkin Trans. 2

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“…p-Cymene-2-sulphonic acid [50] was prepared by the method previously described in the literature [32]. All other chemicals were used as received.…”

Section: Methodsmentioning

confidence: 99%

“…In another example, the esterification of levulinic acid in an excess of ethanol could be promoted using a sulphonated mesoporous carbon supported catalyst (5) [49]. Sulphuric acid in combination with the classic but carcinogenic solvent benzene provided ethyl levulinate in 81% of the theoretical maximum [50].…”

Section: Catalystmentioning

confidence: 99%

“…It has a superior RME to the supported sulphonic acid catalysed methodology but this is due to the large excess of ethanol used in the latter instance [49]. The best mass utilisation comes from the use of sulphuric acid in benzene as a reaction system [50]. Given the precedent of p-cymene as a solvent [32], which should narrowly outperform benzene in esterifications based on polarity arguments [38], the substitution of benzene in sulphuric acid catalysed Fischer esterification would create a more benign but similarly efficient reaction system.…”

Section: Catalystmentioning

confidence: 99%

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Using metrics and sustainability considerations to evaluate the use of bio-based and non-renewable Brønsted acidic ionic liquids to catalyse Fischer esterification reactions

Clark

Farmer

Macquarrie

et al. 2013

sustain chem process

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Background: Ionic liquids have found uses in many applications, one of which is the joint solvation and catalysis of chemical transformations. Suitable Brønsted acidic ionic liquids can be formed by combining lactams with sulphonic acids. This work weighs up the relative benefits and disadvantages of applying these Brønsted acidic ionic liquid catalysts in esterifications through a series of comparisons using green chemistry metrics. Results: A new bio-based ionic liquid was synthesised from N-methyl pyrrolidinone and p-cymenesulphonic acid, and tested as a catalyst in three Fischer esterifications under different conditions. An evaluation of the performance of this Brønsted acidic ionic liquid was made through the comparison to other ionic liquid catalysts as well as conventional homogeneous Brønsted acids.

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“…Many syntheses are described in the literature based on the preparation of 1,4-diketones, which are subsequently cyclized to oxocyclopentenones, or cyclodehydration [30][31][32][33] of γ-methyl-γ-decalactone. Other basic conceptual approaches include molecular rearrangements and those proceeding from dioxocyclopentanes.…”

Section: Introductionmentioning

confidence: 99%

Octanol‐based aroma chemicals, Part 4. A simple synthesis of dihydrojasmone

Zope

Patnekar

Kanetkar

2007

Flavour & Fragrance J

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We have developed a new synthetic method for the preparation of dihydrojasmone via a five-step synthesis from n-octanol. Oxidation of n-octanol gave n-octanal, which after Mannich reaction and hydrogenation yields 2-methyl octanal. Knoevenagel condensation of this substituted aldehyde gave 4-methyldec-3-enoic acid, which on cyclization furnished dihydrojasmone. The process is simple and may be substituted for the existing process of synthesizing dihydrojasmone by the use of 1,4-dicarbonyl ketones.

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The Preparation of Cyclopentenones from Lactones

Cited by 23 publications

References 0 publications

Reactions of some cyclic ethers in superacids

Reactions of some cyclic ethers in superacids

Using metrics and sustainability considerations to evaluate the use of bio-based and non-renewable Brønsted acidic ionic liquids to catalyse Fischer esterification reactions

Octanol‐based aroma chemicals, Part 4. A simple synthesis of dihydrojasmone

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