103-95-7

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 103-95-7 differently. You can refer to the following data:
1. 2-Methyl-3-(p-isopropylphenyl)-propionaldehyde has a strong, flowery odor
2. The commercially available racemate is a colorless to yellowish liquid with an intense floral odor reminiscent of Cyclamen europaeum (cyclamen, sowbread).Production. Two main processes are used for the industrial synthesis of cyclamen aldehyde:1) Alkaline condensation of 4-isopropylbenzaldehyde and propanal results, via the aldol, in the formation of 2-methyl-3-(4-isopropylphenyl)-2-propenal. The unsaturated aldehyde is hydrogenated selectively to the saturated aldehyde in the presence of potassium acetate and a suitable catalyst, such as palladium–alumina:2) Friedel–Crafts reaction of isopropylbenzene and 2-methylpropenal diacetate (methacrolein diacetate) in the presence of titanium tetrachloride/boron trifluoride etherate gives cyclamen aldehyde enolacetate, which is hydrolyzed to aldehyde:Uses. Cyclamen aldehyde is an important component for obtaining special blossomnotes in perfume compositions, particularly the cyclamen type. Because of its fresh, floral aspect, it is also used as the top note in many other blossomfragrances.

Occurrence

Reported found in nutmeg and starfruit.

Uses

Different sources of media describe the Uses of 103-95-7 differently. You can refer to the following data:
1. Cyclamen Aldehyde is a very powerful, floral, green note used in many perfumery applications to blend into fresh, floral, green or ozonic/marine accords. It is an ingredient with growing use and importance in helping to build replacement accords for materials disappearing from the Perfumers’ palette. Cyclamen has good overall stability except in extremes of pH. It has good tenacity and substantivity and represents very good value for money in new creations.
2. Cyclamal, is an ingredient in perfume. It can also be used in the synthesis of Cyclamen Alcohol (C987655).

Preparation

By condensation of cuminic aldehyde and propionaldehyde followed by hydrogenation in the presence of a catalyst

Safety Profile

Moderately toxic by ingestion. A human skin irritant. See also ALDEHYDES. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C13H18O/c1-10(2)13-6-4-12(5-7-13)8-11(3)9-14/h4-7,9-11H,8H2,1-3H3

Upstream product

• 831-97-0 α-methyl-p-isopropylcinnamaldehyde 
• 78-85-3 2-methylpropenal 
• 98-82-8 Isopropylbenzene 
• 61668-36-8 bromo-2 trimethylsilyloxy-1 propene-1 
• 405506-94-7 (4-isopropylbenzyl)magnesium chloride 
• 6839-77-6 Acetat v. 2-Methyl-3-<4-isopropyl-phenyl>-propen-(1)-ol-(1) 
• 67-56-1 methanol 
• 64-17-5 ethanol 
• 71-43-2 benzene 
• 56208-30-1 3t-(4-isopropyl-phenyl)-2-methyl-allyl alcohol 
• 4395-87-3 (4-isopropylphenyl)acetonitrile 
• 1252059-77-0 C₁₇H₂₄O₄ 
• 4756-19-8 2-methyl-3-[4-(methylethyl)phenyl]propanol 
• 10476-95-6 methallylidene diacetate 

Downstream Products

• 26158-51-0 N'-[3-(4-Isopropyl-phenyl)-2-methyl-prop-(E)-ylidene]-hydrazinecarbodithioic acid methyl ester 
• 4756-19-8 2-methyl-3-[4-(methylethyl)phenyl]propanol 
• 191848-12-1 2,2-Difluoro-3-hydroxy-5-(4-isopropyl-phenyl)-4-methyl-pentanoic acid ethyl ester 
• 30127-31-2 1-isobutyl-4-isopropyl-cyclohexane 
• 300393-39-9 2-[3-(p-isopropylphenyl)prol-2-yl]benzimidazole 
• 7149-24-8 2-methyl-3-(4-isopropylphenyl)propanal diethyl acetal 
• 72845-85-3 2-methyl-3-(4-isopropylphenyl)propanal ethylene acetal 

Relevant academic research and scientific papers

Selective Catalytic Hydrogenation in the presence of Lanthanide tris-β-Diketonates as "Protecting" Reagents

The selectivity of >C=C double bonds catalytic hydrogenation increases considerably in the presence of some lanthanide tris-β-diketonates for those unsaturated aldehydes and ketones possessing highly susceptible to reduction carbonyl group.It is a result of the selective co-ordination between the lanthanide complex added and the carbonyl group of a substrate.In most cases the complete protection of carbonyl groups is observed if the complex is added in equimolar amount to the substrate.A number of lanthanum tris-β-diketonates have been tested; the complexes with fluorinated ligands were demonstrated to ensure the highest selectivity of the hydrogenation.The correlation between the constants of equilibrium in reaction mixture and "protecting" activity of the complexes is discussed.A few examples demostrate the practical utilization of the lanthanum tris-β-diketonates to the selective hydrogenation of unsaturated aldehydes and ketones.

Ru-Catalyzed Cross-Dehydrogenative Coupling between Primary Alcohols to Guerbet Alcohol Derivatives: With Relevance for Fragrance Synthesis

A simple method has been developed for the cross dehydrogenative coupling between two different primary alcohols using readily available RuCl2(PPh3)3 as a precatalyst through the borrowing-hydrogen approach. The present methodology is applicable to a large variety of alcohol derivatives including long chain aliphatic alcohols and heteroaryl alcohols. In addition, the methodology was applied in a straightforward protocol to synthesize commercially available fragrances such as Rosaphen and Cyclamenaldehyde in good yields.

Asymmetric α-Allylation of Aldehydes with Alkynes by Integrating Chiral Hydridopalladium and Enamine Catalysis

A palladium-catalyzed asymmetric α-allylation of aldehydes with alkynes has been established by integrating the catalysis of enamine and chiral hydridopalladium complex that is reversibly formed from the oxidative addition of Pd(0) to chiral phosphoric acid. The ternary catalyst system, consisting of an achiral palladium complex, a primary amine, and a chiral phosphoric acid allows the reaction to tolerate a wide scope of α,α-disubstituted aldehydes and alkynes, affording the corresponding allylation products in high yields and with excellent levels of enantioselectivity.

A synthetic route to 4-alkyl-α-methylhydrocinnamylaldehydes

The 4-Alkyl-α-methylhydrocinnamylaldehydes (alkyl-isopropyl, isobutyl, methyl) are frequently used fragrances with desired floral (lilac, cyclamen, lily-of-the-valley) scent. These substances are valued for their good stability in basic solution and, therefore, are frequently used in soaps, detergents, or shampoos. These substances are synthesized by a two-step synthesis involving base catalyzed aldol condensation of 4-alkylbenzaldehyde with propanal followed by selective hydrogenation of the C=C bond. In aldol condensation, selectivity is decreased by formation of undesired products of propanal autocondensation 2-methylpent-2-enal. In this work the reaction conditions for homogenous catalyzed aldol condensation of 4-isobutylbenzadehyde with propanal were tested (catalyst type and amount, molar ratio of reactants, solvent type). Reaction conditions giving the best results (92% conversion, 79% selectivity) were adapted to other 4-alkyl-α-methylcinnamylaldehydes preparation with similar results. In the second step—hydrogenation of aldol product different types of catalyst (nickel, cobalt, palladium or Adkins catalyst), and also different solvents, were tested. Hydrogenation conditions leading to the highest yield (72% selectivity at 95% conversion) were adapted to other 4-alkylhydrocinnamyladehydes with similar results.

Method for synthesizing high-content cyclamen aldehyde spice

The invention discloses a method for synthesizing a high-content cyclamen aldehyde spice, and relates to the technical field of fine chemical engineering. Cumin and propionyl chloride are catalyzed by lewis acid to be subjected to an acylation reaction, and isopropyl benzene acetone is generated; then isopropyl benzene acetone and phosphorus oxychloride are subjected to an acylation reaction, and after distillation and purification, the product, ethyl alcohol, hydrogen and a catalyst are subjected to a hydrogenation reaction; after the reaction is completed, a cyclamen aldehyde crude product is subjected to flashing and fractionation, ethyl alcohol is recycled, and finally spice-grade cyclamen aldehyde is obtained. The content of ortho-position cyclamen aldehyde and cyclamen alcohol in cyclamen aldehyde is controlled to be below 0.5%, and therefore the final product is pure and soft in fragrance and meets the requirements of flavor blending of flavors and fragrances.

Industrial production method of high-content cyclamen aldehyde

The invention discloses a production method of high-content cyclamen aldehyde, relating to the technical field of fine chemical engineering production. After isopropyl benzene and propionyl chloride used as initial raw materials are subjected to acylation reaction, selective hydrogenation is carried out to synthesize cyclamen aldehyde, so the method has the advantages of accessible raw materials and high yield. Ethanol is used as an organic solvent for hydrogenation reaction, thereby overcoming the defects of incomplete reaction or excess hydrogenation and inactivation of the recycled catalyst in the hydrogenation process, and controlling the content of ortho-cyclamen aldehyde of the side reaction at 0.5% or below. Besides, a high-vacuum falling film fractionating tower is used for separating and purifying the cyclamen aldehyde, so that the cyclamen alcohol content in the cyclamen aldehyde finished product is controlled at 0.5% or below; and thus, the singlet content in the final product reaches 98.5% or above, and the final product has pure and soft fragrance and satisfies the requirement for essence blending.

rabbit ear oxaldehyde a method of production

The invention relates to a cyclamen aldehyde production method. The method concretely comprises the following steps: mixing methylacrolein dipropionic acid with isopropyl benzene, slowly adding a titanium tetrachloride and trifluoromethanesulfonic acid mixed solution in a dropwise manner at a low temperature while stirring, reacting, slowly pouring a diluted hydrochloric acid solution into the above obtained reaction solution after completing the reaction, hydrolyzing, taking the obtained organic phase, adding sodium hydroxide and methanol, carrying out a de-esterification reaction, washing by using water after completing the de-esterification reaction, separating the obtained organic layer, and rectifying the above obtained crude product to obtain highly pure cyclamen aldehyde. An innovative titanium tetrachloride and catalytic amount trifluoromethanesulfonic acid double-acid catalysis mode is adopted, the concrete dropwise addition sequence, the reaction time and the temperature are limited, so side reactions are reduced, and the purity of the cyclamen aldehyde is improved; and isopropyl benzene is cheap and easily available, and can be simultaneously used as a solvent and a reactant without adding other solvents, so the method disclosed in the invention has great advantages in cost and three-waste control.

An efficient TiCl4-catalysed method for the synthesis of para-substituted aromatic aldehydes

An efficient and highly selective synthesis of para-substituted aromatic aldehydes has been achieved by TiCl4-catalysed Friedel-Crafts alkylation of monosubstituted benzenes with methacrolein diacetyl acetal.

Cyclamen aldehyde synthesis: Aldol condensation followed by hydrogenation over ruthenium catalyst

Cyclamen aldehyde is a fragrant substance with the scent of cyclamen or lily-of-the-valley. In this work, the desired cyclamen aldehyde was prepared by twostep synthesis. At the first step, aldol condensation of 4-isopropylbenzaldehyde and propanal was carried out. The influence of used catalyst (potassium hydroxide and sodium methoxide) and propanal amount were tested. Propanal was used in excess and it was added to the reaction mixture dropwise (to prevent its self-condensation to 2-methylpent-2-enal). Resulting mixture of 4-isopropylbenzaldehyde and forcyclamen aldehyde was hydrogenated using different Ru/C catalysts. The products detected in hydrogenation reaction mixture were: desired cyclamen aldehyde, cyclamen alcohol and forcyclamen alcohol. The influence of catalyst type and amount, reaction temperature and hydrogen pressure on the reaction course was tested. The highest yield (19.4 %) was obtained using pressure 10 MPa, temperature 110 °C and 2 wt% of catalyst Ru/C.

Microwave-assisted organocatalytic cross-aldol condensation of aldehydes

An environmentally benign organocatalytic cross-aldol condensation of aldehydes under microwave irradiation in the absence of solvent is described. Using pyrrolidine as a catalyst, an efficient and sustainable atom economic method was developed for the cross-aldol condensation of various aldehydes with excellent results. Among the products, jasmine aldehyde, α-hexyl cinnamaldehyde and cyclamen aldehyde, three compounds of great industrial demand, were synthesised.