H-type Zeolite-Catalyzed 1,4-Addition of Benzene Derivatives to Labile Acrolein

Hayashi, Daijiro; Narisawa, Tomoyuki; Masui, Yoichi; Onaka, Makoto

doi:10.1246/bcsj.20150387

Cited by 14 publications

(8 citation statements)

References 45 publications

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“…Purification of the dark red 4‐(4‐hydroxyphenyl)butan‐2‐one raw product by column chromatography followed by recrystallization led to colorless crystalline 4‐(4‐hydroxyphenyl)butane‐2‐one (Figure S4 (NMR spectra), Figure S5 (FT IR spectrum), Figure S6 (Crystals)). This compound is also known from the literature as both natural material and synthetic staff . Furthermore, 4‐(4‐hydroxyphenyl)butane‐2‐one was additionally synthesized in a twostep synthetic pathway described in the supporting information (Scheme S1).…”

Section: Resultsmentioning

confidence: 99%

A Green Step to New Monomers and Their Polymerization

et al. 2020

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Extract obtained from the bark of Betula Pendula was treated with sodium hydroxide solution to obtain 4-(4-hydroxyphenyl) butan-2-one. New (meth)acrylates were synthesized on the basis of 4-(4-hydroxyphenyl)butan-2-one. Free radical polymerization of the new (meth)acrylates was compared with that of commercial monomers (e. g. phenyl(meth)acrylate, 2-phenoxyethyl methacrylate, and benzyl methacrylate) in solution resulting in soluble polymers as expected in all examples. In contrast to this, free radical polymerization of 4-(4-acryloylox-yphenyl)butan-2-one in bulk resulted in a crosslinked material although an extremely high molecular weight soluble polymer was received in case of bulk polymerization of 4-(4-methacryloyloxyphenyl)butan-2-one. The 3-oxobutyl substituent at the phenyl ring of these monomers may influence their radical polymerization. Furthermore, enzyme mediated radical polymerization and photoinitiated polymerization were applied for the polymer synthesis using 4-(4-methacryloyloxyphenyl)butan-2-one.

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Section: Resultsmentioning

confidence: 99%

A Green Step to New Monomers and Their Polymerization

et al. 2020

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“…In addition to spirofused cyclic peroxides, this approach also allows the synthesis of annulated peroxides; for example, the 3‐hydroxymethylated phenol 17 was successfully converted into the seven‐membered cyclic peroxide 19 via the corresponding hydroperoxide 18 (Scheme ) in 41 % overall yield (Figure ).…”

Section: Methodsmentioning

confidence: 99%

Spirofused and Annulated 1,2,4‐Trioxepane‐, 1,2,4‐Trioxocane‐, and 1,2,4‐Trioxonane‐Cyclohexadienones: Cyclic Peroxides with Unusual Ring Conformation Dynamics

et al. 2018

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C3- or C4-hydroxyalkylated phenols are highly reactive towards peroxidation with oxone, which results in the formation of tertiary C3 hydroperoxides. This reaction can also be performed with photochemically generated singlet oxygen. However, other characteristic singlet oxygen reactions do not proceed with caroate. The initially formed hydroperoxides cyclize in the presence of a Lewis acid catalyst based on boron, indium, or iron to give spiroannulated peroxides. These exhibit restricted ring inversion whereas larger nine-membered-ring peroxides are thermally less stable and show higher ring flexibility (according to NMR analysis).

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“…Hayashi and co‐workers reported the Michael addition reaction of phenol with MVK catalysed by H‐type zeolite. While this method has the advantage of avoiding the corrosion of equipment, it suffers from the drawbacks of long reaction time and the use of excessive amounts of phenol 28 …”

Section: Synthesis Of Raspberry Ketonementioning

confidence: 99%

Advances in the synthesis and applications of raspberry ketone: A review

Guo

Chang

Jia

et al. 2021

Flavour & Fragrance J

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Recent advances in the synthesis and applications of raspberry ketone are reviewed in this paper. Different routes to this material including chemical and biotechnological synthetic methods and extraction from natural sources are compared, and the applications of the ketone in flavour and fragrance, pharmaceuticals and in food and tobacco processing are discussed. Synthesis from petrochemical raw materials has the advantages of ready availability of ingredients and well‐understood synthetic steps, but direct synthesis from petrochemicals will eventually be replaced because of low yields and hazardous results to environment. The ketone can be made from natural raw materials, and the methods are promising if their disadvantages such as limited availability and complex, multi‐step reactions and harsh reaction conditions can be overcome. Biotechnological preparation methods have the advantages of reaction specificity, mild reaction conditions, but are limited in applicability because of complications associated with their synthetic and purification procedures at present. With the development of biotechnology, biotechnological preparation methods of the ketone may be the most important route in the future. Direct extraction of the ketone from natural raw materials is possible, but the cost is very high. From the view of syntheses and applications, the research perspectives of raspberry ketone are outlined in the end of this paper, which are the development of green and effective synthetic methods for raspberry ketone from natural raw materials and the preparation and application of raspberry ketone by biotechnological preparation methods.

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H-type Zeolite-Catalyzed 1,4-Addition of Benzene Derivatives to Labile Acrolein

Cited by 14 publications

References 45 publications

A Green Step to New Monomers and Their Polymerization

A Green Step to New Monomers and Their Polymerization

Spirofused and Annulated 1,2,4‐Trioxepane‐, 1,2,4‐Trioxocane‐, and 1,2,4‐Trioxonane‐Cyclohexadienones: Cyclic Peroxides with Unusual Ring Conformation Dynamics

Advances in the synthesis and applications of raspberry ketone: A review

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