5462-06-6

Usage

Uses

Used in Fine Fragrance Industry:
2-METHYL-3-(PARA-METHOXY PHENYL)-PROPANAL is used as a fragrance ingredient for its ability to add a unique licorice and anise note with a slight fruity twist to perfumes and colognes. Its compatibility with floral notes makes it a valuable addition in creating complex and harmonious scents.
Used in Cosmetics Industry:
In the cosmetics industry, 2-METHYL-3-(PARA-METHOXY PHENYL)-PROPANAL is used as a scent component in various products such as lotions, creams, and body care products. Its distinctive aroma adds a pleasant and attractive scent to these products, enhancing the overall sensory experience for the user.

Flammability and Explosibility

Nonflammable

Trade name

Canthoxal (IFF)

InChI:InChI=1/C11H14O2/c1-9(8-12)7-10-3-5-11(13-2)6-4-10/h3-6,8-9H,7H2,1-2H3

Upstream product

• 140-67-0 Estragole 
• 201230-82-2 carbon monoxide 
• 104-46-1 anethole 
• 64506-21-4 (+/-)-2-methyl-3-(p-methoxyphenyl)propanol 
• 64-18-6 formic acid 
• 123-38-6 propionaldehyde 
• 824-94-2 p-methoxybenzyl chloride 
• 2746-25-0 p-Methoxybenzyl bromide 
• 7319-16-6 methyl prop-1-enyl ether 
• 105-13-5 4-Methoxybenzyl alcohol 
• 111-92-2 dibutylamine 
• 67-56-1 methanol 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 52427-11-9 3-(4-methoxyphenyl)-2-methylpropionic acid 
• 1383713-49-2 5-(4-(4-methoxyphenyl)-3-methylbut-1-enyl)benzo[d][1,3]dioxole 
• 1256556-38-3 (1S,3R,R)-3-(1-(4-methoxyphenyl)propan-2-yl)-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine 
• 79253-39-7 (S)-(-)-3-(4-methoxyphenyl)-2-methylpropan-1-ol 
• 152236-02-7 Methanesulfonic acid 1-(benzenesulfinyl-chloro-methyl)-3-(4-methoxy-phenyl)-2-methyl-propyl ester 
• 152236-00-5 1-Benzenesulfinyl-1-chloro-4-(4-methoxy-phenyl)-3-methyl-butan-2-ol 

Relevant academic research and scientific papers

Method for preparing anethol propionaldehyde by anisole

The invention relates to the technical field of organic synthesis, in particular to a method for preparing anethoxyl propionaldehyde by anisole, which comprises anisole and 2 - methylallyl diacetate or anisole. 2 - Methacrolein and acetic anhydride were added to the reaction vessel to catalyze the reaction. Then 1 - acetoxy -2 - methyl -3 - (4 - methoxyphenyl) propylene was added to a reaction vessel carrying an alcoholic solvent and an ester exchange catalyst to carry out an ester exchange reaction. The method solves the problems that the cost of anisic aldehyde or anisaldehyde in the product is high due to the expensive price of anisaldehyde or anethol in the prior art, and anisole is synthesized into anethol propionaldehyde. The synthetic anisanylpropanal has a sufficiently high purity. Can be used for perfumery.

Hydroformylation of natural olefins with the [Rh(COD)(μ-OMe)]2/TPPTS complex in BMI-BF4/toluene biphasic medium: Observations on the interfacial role of CTAB in reactive systems

The complex [Rh(COD)(μ-OMe)]2 in presence of TPPTS (TPPTS = triphenylphosphinetrisulfonate) was evaluated as catalyst precursor for the in situ hydroformylation of natural olefins (eugenol, estragole and safrole) in biphasic media BMIm-BF4/toluene. Under moderate reaction conditions, the substrates showed the following reactivity order: eugenol > estragole > safrole. The rhodium system showed a high activity and selectivity towards the desired aldehydes. It was found that the use of cetyltrimethylammoniun bromide (CTAB) as phase transfer agent inhibits the hydroformylation reaction. The catalytic phase can be recycled up to four times without evident loss of activity or selectivity. In this work we report the use of an ionic liquid with hydrophilic character, without using water in the reaction medium.

Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals

In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.

Anisole: A further step to sustainable hydroformylation

Hydroformylation, also known as the "oxo" process, is a major industrial process that employs rhodium or cobalt catalysts in solution; therefore the solvent of this process is a critical issue for its sustainability. Although several innovative solutions have been proposed recently, traditional fossil-derived solvents dominate the scenario for this reaction. In this paper, we studied a series of solvents considered more sustainable in recent ranks in the hydroformylation of a series of olefins. Anisole, a solvent with an impressive sustainability rank and very scarcely exploited in hydroformylation, proved to be an excellent alternative for this reaction.

Rhodium/Phosphine catalysed selective hydroformylation of biorenewable olefins

This work reports rhodium catalyzed selective hydroformylation of natural olefins like eugenol, estragole, anethole, prenol and isoprenol using biphenyl based Buchwald phosphine ligands (S-Phos (L1), t-Bu XPhos (L2), Ru-Phos (L3), Johnphos (L4) and DavePhos (L5). Ru-Phos (L3) ligand exhibited high impact on the hydroformylation of eugenol providing high selectivity (90%) of linear aldehyde as major product. In addition, internal natural olefins like anethole and prenol provided moderate to high selectivity (65% and 85% respectively) of branched aldehydes as a major products. The various reaction parameters such as influence of ligands, P/Rh ratio, syngas pressure, temperature, time and solvents have been studied. A high activity and selectivity gained on the way to the linear aldehydes it may be due to the bulky, steric cyclohexyl and isopropoxy groups present in L3 phosphine ligand. Moreover, this catalytic system was smoothly converting natural olefins into corresponding linear and branched aldehydes with higher selectivity under the mild reaction conditions.

A method for preparing finocchio yl-propionaldehyde

The invention discloses a preparation method of anisyl propionaldehyde. The preparation method comprises that haloid acid is added into anisyl alcohol, the mixture is stirred and undergoes a reaction at a temperature of 5-20 DEG C for 1-3h, a solvent, alkali powder and a phase-transfer catalyst are added into a reactor, a halide and propionaldehyde are slowly added into the reactor, and the materials in the reactor undergo a reaction at a temperature of 60-110 DEG C for 12-16h to produce a product. The anisyl alcohol sold on the market is used as a raw material and reacts with haloid acid to produce p-methoxybenzyl halide, and the p-methoxybenzyl halide, propionaldehyde, sodium hydroxide powder as a base and toluene as a solvent undergo a reaction in the presence of the phase-transfer catalyst to produce anisyl propionaldehyde. The preparation method is economic and environmentally friendly, is free of high pressure reaction equipment and a noble metal catalyst, has a low cost and simple processes, and allows simple reaction conditions.

Novel preparation method of anisyl propanal

The invention relates to a novel preparation method of anisyl propanal. The method comprises the following steps: adding haloid acid into anisyl alcohol, and stirring at 5-20 DEG C to react for 1-3 hours, thereby obtaining the corresponding anisyl halide; and adding a solvent, a solid weak alkali and propenyl methyl ether into a reactor, slowly adding the halide into the reactor, and reacting at 15-25 DEG C for 4-6 hours, thereby obtaining the product. By using the commercially available anisyl alcohol as the raw material, the anisyl alcohol firstly reacts with the haloid acid to obtain the p-methoxy benzyl halogen, and the obtained p-methoxy benzyl halogen reacts with the propenyl methyl ether by using the solid weak alkali as the alkali and an acetonitrile-water mixed solvent as the solvent to obtain the product anisyl propanal. The method is economical and environment-friendly, does not need any high-pressure reactor or noble metal catalyst, is simple to operate, and has the advantages of low cost and mild reaction conditions.

Support Functionalization with a Phosphine-Containing Hyperbranched Polymer: A Strategy to Enhance Phosphine Grafting and Metal Loading in a Hydroformylation Catalyst

We present the design of a hydroformylation catalyst through the immobilization of air-stable Rh nanoparticles (NPs) on a magnetic support functionalized with a hyperbranched polymer that bears terminal phosphine groups. The catalyst modification with the hyperbranched polymer improved the metal–support interaction, the metal loading, and the catalytic activity. The catalyst was active for the hydroformylation of natural products, such as estragole, and could be used in successive reactions with negligible metal leaching. The phosphine grafting played a key role in the recyclability of Rh NPs under hydroformylation conditions. The catalytic activity was maintained in successive reactions, even if the catalyst was exposed to air during each recovery procedure. The modification of the support with hyperbranched polyester allowed us either to increase the number of Rh active species or to obtain more active Rh species on the catalyst surface.

Rh/Cu2O nanoparticles: Synthesis, characterization and catalytic application as a heterogeneous catalyst in hydroformylation reaction

In this work, we report a rapid protocol for the synthesis of Rh/Cu2O nanoparticles (Rh/Cu2O NPs) in aqueous medium using microwave route. The microwave energy acts as driving force in synthesis which makes the process economical. The obtained nanoparticles were characterized with the help of FEG-SEM, TEM, HRTEM, EDS, XRD, FT-IR and ICP-AES techniques. The prepared Rh/Cu2O nanoparticles gave 100% yield of uniform spherical morphology. This is a simple, inexpensive and time saving protocol for synthesis of Rh/Cu2O nanoparticles than conventional methods. Furthermore, we showed the catalytic application of Rh/Cu2O nanoparticles in hydroformylation reaction for the conversion of 1-hexene to 1-hexanal at mild reaction conditions such as Rh/Cu2O NPs (10 mg), 35 bar pressure of H2/CO at 360 K. The reaction provides 99% conversion and high selectivity (>90%) toward aldehydes with branched aldehyde is a major product. Notably the reaction does not require the any phosphine ligand source, low catalyst loading, low temperature with major advantage of catalyst recyclability.

Phospholes as efficient ancillaries for the rhodium-catalyzed hydroformylation and hydroaminomethylation of estragole

The hydroaminomethylation (HAM) of estragole, a bio-renewable starting material, with di-n-butylamine was studied for the first time resulting in three novel amines. The process consists of the alkene hydroformylation followed by the in situ reductive amination of primarily formed aldehydes. In order to control chemo- and regioselectivities, three classes of phosphorus(III) compounds were employed as ancillaries for rhodium(I) catalysts: phosphine, phosphites and phospholes. Phosphole-promoted systems have showed the best overall performance, being more selective in the hydrofomylation step than non-promoted or phosphite-promoted systems, as well as more efficient in the reductive amination step than the standard triphenylphosphine based system. It has been found that both the double bond isomerization (a concurrent reaction) and the enamine hydrogenation (the last step in the HAM process) are favored by less electron-donating ligands, with phospholes presenting an excellent compromise to ensure high chemoselectivity and reasonably fast formation of target amines.