5689-71-4

Usage

Physical state

Colorless liquid.

Odor

Faint, sweet.

Usage

Commonly used as a fragrance ingredient in perfumes and cosmetics.

Synthesis

Synthesized by the reaction of 4-methoxyphenyl lithium with ethyl chloroacetate, followed by cyclization and subsequent hydrolysis.

Stability

Relatively stable and non-reactive under normal conditions.

Safety precautions

May cause skin and eye irritation upon contact and should be handled with care.

Upstream product

• 135362-69-5 3-(4-methoxybenzyl)oxypropan-1-ol 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 504-63-2 trimethyleneglycol 
• 123-11-5 4-methoxy-benzaldehyde 
• 627-30-5 1-chloro-3-hydroxypropane 
• 24588-72-5 2-(4-methoxyphenyl)-1,3-dithiane 
• 22391-03-3 2-(4-methoxyphenyl)-1,3-oxathiolane 
• 17887-80-8 1,3-bis(trimethylsiloxy)propane 

Downstream Products

• 504-63-2 trimethyleneglycol 
• 24588-72-5 2-(4-methoxyphenyl)-1,3-dithiane 
• 794527-59-6 (2R,3S)-3-[2-(4-Methoxy-benzyloxy)-ethyl]-oxirane-2-carbaldehyde 
• 146986-42-7 ((2S,3S)-3-(2-(4-methoxybenzyloxy)ethyl) oxiran-2-yl)methanol 
• 158817-21-1 (E)-5-(4-methoxybenzyloxy)pent-2-en-1-ol 
• 1376666-04-4 C₂₃H₂₅F₃O₆ 
• 1376666-17-9 C₂₆H₄₂O₅Si 
• 1376666-15-7 C₂₂H₃₆O₄Si 
• 1376666-13-5 C₂₂H₃₈O₄Si 
• 1376666-11-3 (4R,5S,E)-ethyl-5-hydroxy-7-(4-methoxybenzyloxy)-4-methylhept-2-enoate 
• 1005776-31-7 (E)-ethyl-3-((2S,3S)-3-(2-(4-methoxybenzyloxy)ethyl)oxiran-2-yl)acrylates 
• 158817-23-3 (2R,3R)-5-p-methoxybenzyloxy-3-methylpentane-1,2-diol 
• 123-08-0 4-hydroxy-benzaldehyde 
• 22865-60-7 1-(4-methoxybenzyl)-4-methylbenzene 

Relevant academic research and scientific papers

A Direct Method for the Efficient Synthesis of Benzylidene Acetal at Room Temperature

For the first time, a metal-free direct method has been developed for the efficient synthesis of benzylidene acetal at room temperature using Dowex 50WX8 as a solid acid catalyst and Cl3CCN as a novel water scavenger. At room temperature, a wide variety of aryl and α,β-unsaturated aldehydes react readily with functionalized 1,2- and 1,3-diols to furnish the corresponding acetals in very good yields. Labile functional groups, like N-Boc, N-Cbz, -OTBDMS, -OBn, -N3 and acetonide are found to be stable under the reaction conditions. The versatility of this method is further demonstrated with carbohydrate substrates and optically active diols.

Synthesis of a simplified triazole analogue of pateamine A

Pateamine A is a naturally occurring metabolite extracted from the marine sponge Mycale hentscheli. It exhibits potent cytotoxicity towards cancer cell lines and has been shown to target protein translation initiation via inhibition of the function of euk

Cyclopentyl methyl ether-NH4X: A novel solvent/catalyst system for low impact acetalization reactions

Cyclopentyl methyl ether, a low impact ether forming a positive azeotrope with water, was successfully employed as a solvent in the synthesis of 1,3-dioxanes and 1,3-dioxolanes carried out under Dean-Stark conditions by the acetalization of aliphatic and aromatic aldehydes or ketones, employing ammonium salts as environmentally friendly acidic catalysts.

Synthesis of 2-R-1,3-dioxanes, derivatives of functionally substituted aldehydes of vanillin series

By the condensation of substituted aldehydes of vanillin series with 1,3-propanediol in boiling benzene in the presence of sulfo cation exchanger FIBAN K-1 as catalyst functionally 2-R-substituted 1,3-dioxanes were synthesized.

Mesoporous poly-melamine-formaldehyde (mPMF)-a highly efficient catalyst for chemoselective acetalization of aldehydes

A mesoporous poly-melamine-formaldehyde polymer with a high surface area, good porosity and a high density of amine and triazine functional groups was investigated as a highly efficient hydrogen-bonding catalyst. This porous organic polymer was found to be highly effective in catalyzing chemoselective acetalization of aldehydes, without the consumption of any dehydrating agents. The turnover frequency of mesoporous poly-melamine-formaldehyde is hundreds of times higher than melamine monomer, and this high efficiency is due to the high density of aminal (-NH-CH2-NH-) groups and triazine rings in the polymer network, which provides an inherently powerful system with multiple hydrogen bonds. This unique characteristic imparts mesoporous poly-melamine-formaldehyde polymer with a very high activity as a heterogeneous organocatalyst. The polymer is also low cost, and easy to be synthesized and recycled.

Organocatalysis for the acid-free O-arylidenation of carbohydrates

Methyl glycopyranosides of glucose, galactose, and mannose, their 2,3-di-O-benzyl-protected derivatives, as well as the unprotected sugars react with p-methoxybenzaldehyde dimethyl acetal (3) and with benzaldehyde dimethyl acetal (7) as reagents in the presence of thiourea 1 or squaramide 2 as the organocatalyst to afford regioselectively 4,6-O-arylidenated derivatives 5 and 8. With an excess amount of 3 or 7, diarylidenated derivatives are also obtained. In situ formation of acetals of type 3 and 7 from corresponding aldehydes 10 and 13 in the presence of an orthoester and organocatalyst 1 or 2 can be used to generate 5 and 8 directly from the aldehydes. Some substrates also lead to mixed orthoesters with this procedure. The reaction courses are discussed. A squaramide catalyzes the 4,6-O-arylidenation of glucose, mannose, and galactose with the use of arenecarbaldehyde dimethyl acetals or arenecarbaldehydes and orthoesters as the reagents. Glycoside derivatives also undergo this reaction. Copyright

A METHOD OF ACETALIZING AN ALDEHYDE

A method of acetalizing an aldehyde comprising reacting said aldehyde with an alcohol in the presence of a polymeric catalyst to form an acetal wherein the polymeric catalyst is a mesoporous poly-melamine-formaldehyde polymer.

Synthesis of the C1-C9 fragment of the potent antitumor agent dictyostatin

We describe herein a short and efficient synthesis of the C1-C9 fragment of the potent antitumor agent dictyostatin. Notable features of this approach include a Sharpless asymmetric epoxidation followed by epoxide opening under Myashita's conditions to in

2,3-dichloro-5,6-dicyano-1,4-benzoquinone-catalyzed teactions employing MnO2 as a stoichiometric oxidant

Several oxidative reactions can be effected with MnO2 in the presence of substoichiometric quantities of DDQ. These transformations include oxidative cyclization, deprotection, and dehydrogenation reactions. The use of MnO2 as a terminal oxidant for DDQ-mediated reactions is attractive based on economical and environmental factors.

Acetalization of carbonyl compounds catalyzed by bismuth triflate under solvent-free conditions

Carbonyl compounds were converted to the corresponding 1,3-dioxolanes and 1,3-dioxanes with ethylene glycol and 1,3-propandiol in the presence of bismuth triflate under solvent-free conditions. In addition, high chemoselective protection of aldehydes in the presence of ketones has been achieved.