772-00-9

Usage

Chemical Properties

CLEAR SLIGHTLY YELLOW LIQUID

Synthesis Reference(s)

Tetrahedron Letters, 22, p. 723, 1981 DOI: 10.1016/0040-4039(81)80133-5

InChI:InChI=1/C10H12O2/c1-2-4-9(5-3-1)10-6-7-11-8-12-10/h1-5,10H,6-8H2

Upstream product

• 110-88-3 1,3,5-Trioxan 
• 100-42-5 styrene 
• 50-00-0 formaldehyd 
• 98-85-1 1-Phenylethanol 
• 75-07-0 acetaldehyde 
• 145372-92-5 4-phenyl-4H-1,3-dioxin 
• 78-84-2 isobutyraldehyde 
• 123-63-7 paracetaldehyde 
• 637-50-3 1-phenylpropene 
• 617-86-7 triethylsilane 
• 36626-52-5 1-phenylpropane-1,3-diyl diformate 
• 4850-49-1 1-phenyl-1,3-propanediol 
• 13865-50-4 methoxymethyl phenyl sulfide 
• 17763-67-6 Phenyl triflate 

Downstream Products

• 122-97-4 3-Phenyl-1-propanol 
• 14155-36-3 (+/-)-(1,3-dichloropropyl)benzene 
• 14593-04-5 3-amino-3-phenyl-1-propanol 
• 499238-38-9 1,5-diacetoxy-5-phenyl-2-oxapentane 
• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 
• 873-49-4 cyclopropylbenzene 
• 3524-55-8 4-phenyl-1,3-dioxan-2-one 
• 499238-37-8 3,4-diaza-2,2-dimethyl-7-phenyl-1,6,10-trioxaspiro[5,4]dec-3-ene 
• 499238-39-0 hydrazinecarboxylic acid 3-hydroxy-3-phenyl-propyl ester 
• 499238-41-4 3-isopropylidene carbazic acid 3-hydroxy-3-phenylpropyl ester 
• 107796-30-5 4-phenyl-1,3-dioxane 
• 107796-29-2 (R)-4-phenyl-1,3-dioxane 
• 62296-02-0 1-(acetoxymethoxy)-3-acetoxy-1-phenylpropane 
• 96854-34-1 (S)-3-phenyl-1,3-propanediol 

Relevant academic research and scientific papers

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.

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.

Chemoselective Deoxygenation of 2° Benzylic Alcohols through a Sequence of Formylation and B(C6F5)3-Catalyzed Reduction

A sequence of formylation and B(C6F5)3-catalyzed reduction of the resulting formate with Et3SiH enables the chemoselective deoxygenation of secondary benzylic alcohols. Primary benzylic and tertiary non-benzylic alcohols are not reduced by this protocol. The formyl group fulfills a double role as activator and self-sacrificing protecting group. The deoxygenation of these formates is fast and can be carried out in the presence of other potentially reducible groups. Neighboring-group participation was found in the deoxygenation of certain diol motifs.

Synthesis of ethers and cyclic acetals in the presence of CBV-720 zeolite

СBV-720 zeolite was compared to H-Beta zeolite and KU-2 cation-exchange resin in the catalytic performance in addition of alcohols to norbornene, in condensation of aldehyde and ketone with di- and triols, and in the Prins reaction of olefins with formaldehyde. These reactions, when performed on СBV-720 zeolite, occur 1.5–2 times faster than on the other catalysts. The corresponding ethers and cyclic acetals were synthesized.

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.]

Methylene acetal formation from 1,2- and 1,3-diols using an O, S -acetal, 1,3-dibromo-5,5-dimethylhydantoin, and BHT

A mild and efficient method for formation of methylene acetals from 1,2- and 1,3-diols using methoxymethylphenylsulfide, 1,3-dibromo-5,5- dimethylhydantoin (DBDMH), and dibutylhydroxytoluene (BHT) is described. The use of BHT in this process suppresses side reactions and enables high-yielding formation of methylene acetals of various diols, including carbohydrate-type substrates.

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.

Investigation of Prins reaction for the synthesis of 2, 4-disubstituted tetrahydropyran derivatives and 1, 3-dioxanes using polyaniline supported acid as reusable catalyst

The Prins cyclization of homoallyl alcohol with a variety of aldehydes were observed under reflux condition in dichloromethane using both polyaniline supported TsOH (PANI-TsOH) and FeCl3 (PANI- FeCl3) as reusable acid catalysts with the formation of 2,4-disubstituted tetrahydropyran ether as single product. In case of 4-, 3- and 2- nitro benzaldehydes, the reaction generated acetal of the aldehyde and homoallylic alcohol as single product. Additionally, both catalysts were investigated for the synthesis of 1, 3-dioxane in dichloromethane under reflux and at ambient temperature Indian Academy of Sciences.

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.

Synthesis of 1,3-dioxanes catalyzed by TsOH-SiO2 under solvent-free conditions

Silica-supported p-toluene sulfonic acid is found to be an excellent catalyst for the Prins reaction to produce 1,3-dioxanes in good yields from olefins and aliphatic aldehydes in dichloromethane at room temperature and solventless microwave irradiation within a short reaction time. Copyright Taylor & Francis Group, LLC.