128994-23-0

Upstream product

• 50-00-0 formaldehyd 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 

Downstream Products

• 33348-72-0 3-hydroxy-1-(4'-methylphenyl)propan-1-one 

Relevant academic research and scientific papers

Cation-Exchanged Montmorillonite (Mn+-Mont)-Catalyzed Prins Reaction

The Prins reaction of styrenes with paraformaldehyde or 1,3,5-trioxane in toluene in the presence of cation-exchanged montmorillonite (Mn+-mont), which worked as a Bronsted acid catalyst, at 80°C produced 4-aryl-1,3-dioxanes selectively in up to 99% isolated yield with a turnover number of up to 5.9×102. Among the examined 21 Mn+-monts, Ce3+- and Fe3+-monts were revealed to be quite effective. Regeneration of the catalyst was confirmed with the Ce3+-mont, which could be effectively recycled at least three times. Many lanthanide metal ion-exchanged montmorillonites (Ln3+-monts) were prepared and characterized by X-ray powder diffraction (XRD) and temperature-programmed desorption of ammonia gas (NH3-TPD) methods.

ZnAlMCM-41: a very ecofriendly and reusable solid acid catalyst for the highly selective synthesis of 1,3-dioxanes by the Prins cyclization of olefins

The Prins cyclization of styrene (SE) with paraformaldehyde (PFCHO) was conducted with mesoporous ZnAlMCM-41 catalysts for the synthesis of 4-phenyl-1,3-dioxane (4-PDO) using a liquid phase heterogeneous catalytic method. For a comparison study, the Prins cyclization reaction was also conducted over different nanoporous catalysts,e.g.mesoporous solid acid catalysts, AlMCM-41(21) and ZnMCM-41(21), and microporous catalysts, USY, Hβ, HZSM-5, and H-mordenite. The recyclable mesoporous ZnAlMCM-41 catalysts were reused in this reaction to evaluate their catalytic stabilities. Since ZnAlMCM-41(75) has higher catalytic activity than other solid acid catalysts, washed ZnAlMCM-41(75)/W-ZnAlMCM-41(75) was prepared using an efficient chemical treatment method and used with various reaction parameters to find an optimal parameter for the highly selective synthesis of 4-PDO. W-ZnAlMCM-41(75) was also used in the Prins cyclization of olefins with PFCHO and formalin (FN, 37% aqueous solution of formaldehyde (FCHO)) under different reaction conditions to obtain 1,3-dioxanes, which are widely used as solvents or intermediates in organic synthesis. Based on the nature of catalysts used under different reaction conditions, a reasonable plausible reaction mechanism for the Prins cyclization of SE with PFCHO is proposed. Notably, it can be seen from the catalytic results of all catalysts that the W-ZnAlMCM-41(75) catalyst has higher 4-PDO selectivity with exceptional catalytic activity than other microporous and mesoporous catalysts.

Highly efficient synthesis of 1,3-dioxanes via prins reaction in bronsted-acidic imidazolium ionic liquid

The high-yielding synthesis of a wide variety of 1,3-dioxanes via the Prins reaction under mild conditions has been demonstrated using Bronsted- acidic imidazolium ionic liquid [bmim(SO3H)][OTf] or bmimOTf. The use of ionic liquid makes this synthesis simple, convenient, cost-effective, and environmentally friendly. Furthermore, bmimOTf was conveniently separated from the products and can be easily recycled for the Prins reaction with excellent yields. This method works well with a variety of aliphatic aldehydes including formaldehyde, acetaldehyde, propionaldehyde, and cyclohexanecarboxaldehyde. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Prins cyclization of styrenes or acetophenone catalyzed by DBSA in water

Dodecylbenzenesulfonic acid (DBSA) was proved to be an efficient catalyst for Prins cyclization of styrenes and formaldehyde or acetaldehyde in water. A tandem dehydration/ Prins cyclization reaction using a tertiary alcohol and formaldehyde as substrates proceeded very well by using DBSA as catalyst. Acetophenone, which is less reactive compared with styrene, can also react with formaldehyde when catalyzed by DBSA in water to afford 1,3-dioxan-5- ylphenylmethanone in good yield. Copyright Taylor & Francis Group, LLC.

Heteropolyacid salts of N-methyl-2-pyrrolidonium as highly efficient and reusable catalysts for Prins reactions of styrenes with formalin

New organic heteropolyacid (HPA) salts prepared by exchanging counter protons of Keggin HPAs with N-methyl-2-pyrrolidonium proved to be highly efficient, conveniently recoverable, and steadily reusable heterogeneous catalysts for the organic solvent-free Prins reactions of styrenes with formalin. The Royal Society of Chemistry.

Selectivity enhancement of silica-supported sulfonic acid catalysts in water by coating of ionic liquid

Coating of silica-supported sulfonic acid catalysts with hydrophobic ionic liquid leads to a significant improvement of catalyst selectivity. Many organic reactions, including Prins cyclization, cycloaddition of epoxide to aldehyde, and dehydrative etherification of secondary benzyl alcohols, proceed well in formalin or pure water. In particular, tandem dehydration/Prins cyclization reactions of tertiary and secondary alcohols with formaldehyde were developed for the first time.

Novel hydrophobic Bronsted acidic ionic-liquids as efficient and reusable catalysts for organic reactions in water

Novel Hydrophobic Bronsted acidic ionic liquids (HBAIL) were prepared and utilized as acid catalysts in organic reactions in water. HBAILs were demonstrated, for the first time, to be effective catalysts for Prins cyclization of styrene derivatives in water with a formaldehyde water solution. Many styrene derivatives could be successfully converted to the corresponding 1,3-dioxanes. Other dehydration reactions also proceeded well using HBAILs in water. After reactions, HBAILs could be easily recovered and reused without significant loss of activity. Copyright

Facile and efficient method for the Prins reactions of styrenes and homoallyl alcohols to 1,3-dioxanes and 4-tetrahydropyranols using bismuth(III) triflate

Bismuth(III) inflate has been found to be an efficient catalyst for the Prins reactions of styrenes and homoallyl alcohols, the reaction proceeds rapidly and affords the corresponding 1,3-dioxanes and tetrahydropyran-4-ol in good yields. Scope and limitations of the styrenes and homoallyl alcohols are reported. Copyright Taylor & Francis, Inc.

Selective Prins reaction of styrenes and formaldehyde catalyzed by 2,6-Di-tert-butylphenoxy(difluoro)borane

The sterically congested Lewis acid 1 was used as a catalyst in the Prins reaction of various styrenes and formaldehyde. 4-Aryl-1,3-dioxanes 5 were selectively formed as the exclusive products of the reaction with styrenes 4a-i and vinylthiophenes 4j-k. The reaction proceeded in most cases with good to excellent yields (55-99%). Styrenes which carried a strongly electron-withdrawing group (CN, CO2Me) did not react. The reaction with β-alkylstyrenes 6 was successful for the methyl substituted substrate 6a and yielded (88%) trans-5-methyl-4-phenyl-1,3-dioxane (7a) preferentially (dr = 75:25). For steric reasons, other β-alkylstyrenes 6b-d did not react. The remarkable stereodiscrimination attained by catalyst 1 was employed in the regioselective transformation of 4-propenylstyrene (10) to dioxane 11 (83% yield).

First TaCl5-SiO2 catalyzed prins reaction : Comparative study of conventional heating vs microwave irradiation

TaCl5-SiO2 catalyzed Prins reaction has been achieved for the first time using microwave irradiation.