20238-83-9

Usage

Uses

As the specific uses or biological activities of 3-(4-HYDROXY-PHENYL)-PROPIONALDEHYDE are not widely reported in the literature, it is difficult to provide a comprehensive list of its applications. However, based on its chemical structure and the properties of phenylpropanoids in general, it can be inferred that 3-(4-HYDROXY-PHENYL)-PROPIONALDEHYDE may have potential applications in various industries, such as:
Used in Pharmaceutical Industry:
3-(4-HYDROXY-PHENYL)-PROPIONALDEHYDE could be used as a chemical intermediate for the synthesis of pharmaceutical compounds, given its reactivity and the presence of functional groups that can be further modified.
Used in Chemical Research:
3-(4-HYDROXY-PHENYL)-PROPIONALDEHYDE may be used as a research compound in the study of phenylpropanoid chemistry, to explore its reactivity and potential interactions with other molecules.
Used in Material Science:
Due to its unique structure, 3-(4-HYDROXY-PHENYL)-PROPIONALDEHYDE could potentially be used in the development of new materials with specific properties, such as in polymer chemistry or as a component in the synthesis of advanced materials.

InChI:InChI=1/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h3-7,11H,1-2H2

Upstream product

• 540-38-5 p-Iodophenol 
• 107-18-6 allyl alcohol 
• 5406-18-8 3-(p-methoxyphenyl)-1-propanol 
• 20401-88-1 3-(4-methoxyphenyl)propional 
• 107-02-8 acrolein 
• 108-95-2 phenol 
• 25743-64-0 3-(4-acetoxyphenyl)acrylic acid ethyl ester 
• 878-00-2 4-formylphenyl acetate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 100613-03-4 3-(4-acetoxy-phenyl)-propionic acid ethyl ester 
• 20649-40-5 (E)-4-(3-hydroxyprop-1-enyl)phenol 
• 103-90-2 4-acetaminophenol 
• 2538-87-6 trans-p-hydroxycinnamaldehyde 
• 5597-50-2 3-(4-hydroxyphenyl)propionic acid methyl ester 

Downstream Products

• 245650-20-8 N-[N-[3-(4-hydroxyphenyl) propyl]-L-α-aspartyl]-L-phenylalanine 1-methyl ester 
• 147974-20-7 3-[4-(tert-butyl-dimethyl-silanyloxy)phenyl]propionaldehyde 

Relevant academic research and scientific papers

Hydroformylation of monosubstituted alkenes catalyzed by W-Rh bimetallic complex

By using a heterobimetallic catalyst, (CO)4(PEtPh 2)-W(μ-PPh2)Rh(CO)(PPh3), chemoselective hydroformylation of monosubstituted alkenes proceeds efficiently at room temperature under atmospheric pressure of CO/H

Synthesis of rac-ɑ-aryl propionaldehydes via branched-selective hydroformylation of terminal arylalkenes using water-soluble Rh-PNP catalyst

This work detailed the preparation of a class of water-soluble PNP ligands that differed by the nature of the substitute on phenyl ring of ligands. These ligands were incorporated into water-soluble rhodium-PNP complex catalysts that were used to regioselective hydroformylation of a series of terminal arylalkenes, providing efficient access to rac-α-aryl propionaldehydes in good to excellent yield (up to 97%) and branched-regioselectivity (up to 40:1 b/l ratio). Furthermore, gram-scale and diverse synthetic transformation demonstrated synthetic application of this methodology for non-steroidal antiinflammatory drugs.

Heck arylation of allyl alcohol catalyzed by Pd(0) nanoparticles

Pd(0) nanoparticles ca. 2 nm in diameter were obtained by the reduction of PdCl2 and Pd(OAc)2 in water at 80 °C in the presence of a PVP-stabilizing polymer. Pd(0) NPs were successfully used in the Heck coupling of allyl alcohol with iodo- and bromobenzenes. Iodobenzenes reacted under solventless conditions or in DMF solution producing 3-arylpropanals and 2-arylpropanals as the main products. The same products were obtained in the reaction of bromobenzene in TBAB as the reaction medium. The stability of Pd(0) NPs was evidenced in recycling experiments. Similar Heck coupling results were also obtained with the palladium compounds PdCl2(cod) and Pd(OAc)2 under the same conditions.

Switchable Site-Selective Catalytic Carboxylation of Allylic Alcohols with CO2

A switchable site-selective catalytic carboxylation of allylic alcohols has been developed in which CO2 is used with dual roles, both facilitating C?OH cleavage and as a C1 source. This protocol is characterized by its mild reaction conditions, absence of stoichiometric amounts of organometallic reagents, broad scope, and exquisite regiodivergency which can be modulated by the type of ligand employed.

Enantioselective β-Alkylation of Aldehydes through an Organocatalyzed C-C Bond-Scission Reaction

A novel organocatalyzed C-C bond-scission reaction of saturated aldehydes containing a suitable leaving group at the β-position was used for the in situ formation of iminium intermediates, which were then captured by nucleophiles to achieve a direct enantioselective β-alkylation of aldehydes. Within short reaction times, the corresponding β-alkylated aldehyde products were obtained in high yields (48-87%) and with excellent enantioselectivities (84-98%).

H-type zeolite-catalyzed 1,4-addition of benzene derivatives to labile acrolein

The 1,4-addition of benzene derivatives to acrolein is a straightforward way to synthesize 3-arylpropanals. A survey of acid catalysts for the 1,4-addition of methoxy-substituted benzenes to acrolein revealed that H-Beta and H-Y were the most suitable catalysts. We hypothesized three side-reactions: (1) the double 1,4-addition of acrolein to the starting benzene derivatives, (2) the Friedel-Crafts-type alkylation to the desired product, and (3) the self-polymerization of acrolein. The type (3) side-reaction was inhibited by two different methods which kept the concentration of acrolein low in the reaction mixture or in the zeolite pores. First, acrolein monomers were in situ generated through the gradual monomerization of an acrolein cyclic trimer. Second, using a reaction solvent lowered the acrolein concentration in the zeolite pores due to the competitive adsorption. We discovered that the content of monomeric acrolein in a solvent was closely related to the polarity of the solvent. Actually, both methods improved the yields for the 1,4-additions of 1,3-dimethoxybenzene to acrolein. Other electron-rich benzene derivatives, such as phenol and N, N-dimethylaniline, were also applicable to the 1,4-addition reactions.

One-Pot, Enantioselective Synthesis of 2,3-Dihydroazulen-6(1H)-one: A Concise Access to the Core Structure of Cephalotaxus Norditerpenes

A one-pot enantioselective synthesis of cis-substituted 2,3-dihydroazulen-6(1H)-one is described. In this cascade reaction, an organocatalyzed asymmetric Michael reaction furnishes a highly optically pure nitrobutylphenol intermediate, which is converted into an annulated tropone species by sequential oxidative dearomatization, conjugate addition, electrocyclic ring opening and nitrous acid elimination in the same reaction vessel. Both aliphatic and aromatic nitroalkenes are good substrates for the one-pot reaction, and this protocol appears to be general for various phenylpropionaldehydes as well. In the case of asymmetrically substituted phenylpropionaldehydes, the regioselectivity is likely determined by both the steric and electronic properties of the substituents. This methodology is successfully applied to the synthesis of the tricyclic core structure of Cephalotaxus norditerpenes.

Organocatalytic, Enantioselective Synthesis of Cyclohexadienone Containing Hindered Spirocyclic Ethers through an Oxidative Dearomatization/Oxa-Michael Addition Sequence

An unprecedented enantioselective oxa-Michael reaction of α-tertiary alcohols using cinchona-alkaloid-based chiral bifunctional squaramide catalysts is reported. An oxidative dearomatization of phenol followed by an enantioselective oxa-Michael addition s

CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF

The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.

Scope and mechanism in palladium-catalyzed isomerizations of highly substituted allylic, homoallylic, and alkenyl alcohols

Herein we report the palladium-catalyzed isomerization of highly substituted allylic alcohols and alkenyl alcohols by means of a single catalytic system. The operationally simple reaction protocol is applicable to a broad range of substrates and displays a wide functional group tolerance, and the products are usually isolated in high chemical yield. Experimental and computational mechanistic investigations provide complementary and converging evidence for a chain-walking process consisting of repeated migratory insertion/β-H elimination sequences. Interestingly, the catalyst does not dissociate from the substrate in the isomerization of allylic alcohols, whereas it disengages during the isomerization of alkenyl alcohols when additional substituents are present on the alkyl chain.