5663-20-7

Upstream product

• 50-00-0 formaldehyd 
• 637-50-3 1-phenylpropene 
• 873-66-5 1-propenylbenzene 
• 93-54-9 1-Phenyl-1-propanol 

Downstream Products

• 22436-06-2 2-methyl-3-phenylpropanol 
• 99865-09-5 4-methyl-3-phenyl-dihydro-furan-2-one 
• 16735-22-1 3-hydroxy-2-methylpropiophenone 

Relevant academic research and scientific papers

The Catalytic Asymmetric Intermolecular Prins Reaction

Despite their significant potential, catalytic asymmetric reactions of olefins with formaldehyde are rare and metal-free approaches have not been previously disclosed. Here we describe an enantioselective intermolecular Prins reaction of styrenes and paraformaldehyde to form 1,3-dioxanes, using confined imino-imidodiphosphate (iIDP) Br?nsted acid catalysts. Isotope labeling experiments and computations suggest a concerted, highly asynchronous addition of an acid-activated formaldehyde oligomer to the olefin. The enantioenriched 1,3-dioxanes can be transformed into the corresponding optically active 1,3-diols, which are valuable synthetic building blocks.

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.]

Iodine as a mild and versatile reagent for the synthesis of 1,3-dioxane derivatives via the Prins reaction

Iodine is found to be an effective reagent for the cross-coupling of olefins with aldehydes under mild conditions to produce 4-substituted 1,3-dioxane derivatives in excellent yields and in short reaction times with high selectivity. The use of iodine makes this procedure simple, convenient, cost-effective and practical. This method works not only with formaldehyde but also with acetaldehyde, propionaldehyde and cyclohexanecarboxaldehyde.

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.

SUR UN CONCEPT ORIGINAL : LA CATALYSE TRIPHASIQUE ET LES ECHANGEURS DE CATIONS

The condensation in triphase process of aqueous formaldehyde with aromatic alkanes dissolved in an organic solvent is possible in the presence of polystyrene sulfonic acid resin.