1949-41-3

Usage

Uses

Used in Pharmaceutical Industry:
α-Methylbenzenebutyric acid is used as a chiral building block for the synthesis of various pharmaceuticals and biologically active molecules. Its unique structure and properties make it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Medical Research:
α-Methylbenzenebutyric acid is utilized in medical research for its anti-inflammatory, anti-tumor, and anti-cancer properties. These characteristics are being explored for potential treatments and therapies in oncology and other medical disciplines.
Used in Flavor and Fragrance Industry:
As a precursor for the synthesis of synthetic flavors and fragrances, α-Methylbenzenebutyric acid is used in the food and cosmetic industries. Its ability to contribute to the creation of specific scents and tastes makes it a useful component in these sectors.
Used in Cosmetic Industry:
α-Methylbenzenebutyric acid is also used in the cosmetic industry, where its properties may contribute to the development of products with specific fragrances or other sensory attributes, enhancing the consumer experience.

InChI:InChI=1/C11H14O2/c1-9(11(12)13)7-8-10-5-3-2-4-6-10/h2-6,9H,7-8H2,1H3,(H,12,13)

Upstream product

• 1771-65-9 2-methyl-4-oxo-4-phenylbutanoic acid 
• 15732-75-9 3-benzoyl-2-methylenepropionic acid 
• 14307-99-4 ethyl 2-methyl-4-phenyl butyrate 
• 4371-01-1 β-Phenaethyl-methyl-malonsaeure 
• 100-42-5 styrene 
• 802294-64-0 propionic acid 
• 84229-07-2 2-benzylsulfonyl-2-methyl-4-phenylbutyric acid 
• 582-62-7 3-methyl-1-phenylbutan-1-one 
• 7647-01-0 hydrogenchloride 
• 100-44-7 benzyl chloride 
• 82236-51-9 benzyl 2-benzylsulfonyl-4-phenylbutyrate 
• 4100-80-5 2-methylsuccinic anhydride 
• 14308-32-8 2,2-diethoxy-3-methyl-5-phenyl-2,3-dihydro-furan 
• 71-43-2 benzene 

Downstream Products

• 1590-08-5 2-methyl-1-tetralone 
• 242483-39-2 2-methyl-4-phenyl-butyryl chloride 
• 41927-30-4 2-methyl-4-phenylbutan-1-ol 
• 41927-29-1 (S)-2-methyl-4-phenyl-1-butyric acid 
• 80651-37-2 (R)-(-)-2-methyl-4-phenylbutyric acid 
• 38795-58-3 2-methyl-4-phenylbutyric acid methyl ester 
• 7469-77-4 2-methylnaphthalen-1-ol 
• 20601-20-1 benzoic acid-(2-methyl-[1]naphthyl ester) 
• 27491-34-5 (S)-2-methyl-4-cyclohexyl-butyric acid 
• 5195-30-2 3-methyl-5-phenyl-2-pentanone 
• 36748-51-3 2,3-Dimethyl-5-phenyl-2-pentanol 
• 1361152-13-7 tert-butyl 2-methyl-4-phenylbutaneperoxoate 
• 132665-55-5 1-(3-fluorobutyl)benzene 
• 1425052-50-1 2-phenethyl-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-5-(triisopropylsilyl)pent-4-ynamide 

Relevant academic research and scientific papers

Pd-Catalyzed Regioselective Branched Hydrocarboxylation of Terminal Olefins with Formic Acid

A regioselective Pd-catalyzed hydrocarboxylation of terminal olefins with HCOOH is described. A wide variety of branched carboxylic acids can readily be obtained with high regioselectivities under mild reaction conditions. The reaction is operationally simple and requires no handling of toxic CO. The ligand and LiCl are important factors for reaction reactivity and selectivity.

Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C-H/C-H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F

The development of practical C-H/C-H coupling reactions remains a challenging yet appealing synthetic venture because it circumvents the need to prefunctionalize both coupling partners for the generation of C-C bonds. Herein we report a cyclative C(sp3)-H/C(sp2)-H coupling reaction of free aliphatic acids enabled by a cyclopentane-based mono-N-protected β-amino acid ligand. This reaction uses inexpensive sodium percarbonate (Na2CO3·1.5H2O2) as the sole oxidant and generates water as the only byproduct. A range of biologically important scaffolds, including tetralins, chromanes, and indanes, can be easily prepared by this protocol. Finally, the synthetic application of this methodology is demonstrated by the concise total synthesis of (±)-russujaponol F in a four-step sequence starting from readily available phenylacetic acid and pivalic acid through sequential functionalizations of four C-H bonds.

Intramolecular Oxidative Coupling between Unactivated Aliphatic C-H and Aryl C-H Bonds

Direct oxidative coupling of different inert C-H bonds is the most straightforward and environmentally benign method to construct C-C bonds. In this paper, we developed a Pd-catalyzed intramolecular oxidative coupling between unactivated aliphatic and aryl C-H bonds. This chemistry showed great potential to build up fused cyclic scaffolds from linear substrates through oxidative couplings. Privileged chromane and tetralin scaffolds were constructed from readily available linear starting materials in the absence of any organohalides and organometallic partners.

Palladium-Catalyzed C(sp3)-H Nitrooxylation with tert-Butyl Nitrite and Molecular Oxygen

Herein, we report a Pd(II)-catalyzed nitrooxylation of unactivated methyl C(sp3)-H bonds using commercial available and easily manageable tert-butyl nitrite as the precursor of ONO2 radical under aerobic conditions. Environmentally benign molecular oxygen is used to initiate the generation of active radical reactant; it is also used as the terminal oxidant. A broad range of nitrooxylated aliphatic carboxamides were prepared in moderate to good yields under mild conditions.

Pd(ii)/Zn co-catalyzed chemo-selective hydrogenation of α-methylene-γ-keto carboxylic acids

An efficient Pd/Zn co-catalyzed chemo-selective hydrogenation of α-methylene-γ-keto carboxylic acids is described. This methodology offers a divergent synthesis of α-methyl-γ-keto carboxylic acids, α-methylcarboxylic acids, and lactones starting from α-me

Synthesis of Carboxylic Acids by Palladium-Catalyzed Hydroxycarbonylation

The synthesis of carboxylic acids is of fundamental importance in the chemical industry and the corresponding products find numerous applications for polymers, cosmetics, pharmaceuticals, agrochemicals, and other manufactured chemicals. Although hydroxycarbonylations of olefins have been known for more than 60 years, currently known catalyst systems for this transformation do not fulfill industrial requirements, for example, stability. Presented herein for the first time is an aqueous-phase protocol that allows conversion of various olefins, including sterically hindered and demanding tetra-, tri-, and 1,1-disubstituted systems, as well as terminal alkenes, into the corresponding carboxylic acids in excellent yields. The outstanding stability of the catalyst system (26 recycling runs in 32 days without measurable loss of activity), is showcased in the preparation of an industrially relevant fatty acid. Key-to-success is the use of a built-in-base ligand under acidic aqueous conditions. This catalytic system is expected to provide a basis for new cost-competitive processes for the industrial production of carboxylic acids.

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.

Cooperative iodine and photoredox catalysis for direct oxidative lactonization of carboxylic acids

A new method for the formation of γ- and δ-lactones from carboxylic acids through direct conversion of benzylic C-H to C-O bonds is described. The reaction is conveniently induced by visible light and relies on a mild cooperative catalysis by the combination of molecular iodine and an organic dye.

1-Aminopyridinium Ylides as Monodentate Directing Groups for sp3 C-H Bond Functionalization

1-Aminopyridinium ylides are efficient directing groups for palladium-catalyzed β-arylation and alkylation of sp3 C-H bonds in carboxylic acid derivatives. The efficiency of these directing groups depends on the substitution at the pyridine moiety. The unsubstituted pyridine-derived ylides allow functionalization of primary C-H bonds, while methylene groups are unreactive in the absence of external ligands. 4-Pyrrolidinopyridine-containing ylides are capable of C-H functionalization in acyclic methylene groups in the absence of external ligands, thus rivaling the efficiency of the aminoquinoline directing group. Preliminary mechanistic studies have been performed. A cyclopalladated intermediate has been isolated and characterized by X-ray crystallography, and its reactivity was studied.

CATALYTIC CARBOXYLATION OF ACTIVATED ALKANES AND/OR OLEFINS

The present invention relates to a method of reacting starting materials with an activating group, namely alkanes carrying a leaving group and/or olefins, with carbon dioxide under transition metal catalysis to give carboxyl group-containing products. It is a special feature of the method of the present invention that the carboxylation predominantly takes place at a preferred position of the molecule irrespective of the position of the activating group. The carboxylation position is either an aliphatic terminus of the molecule or it is a carbon atom adjacent to a carbon carrying an electron withdrawing group. The course of the reaction can be controlled by appropriately choosing the reaction conditions to yield the desired regioisomer.