92-48-8

Usage

Uses

Used in Flavor Industry:
6-Methylcoumarin is used as a flavoring agent for creating natural and artificial flavors, particularly for coconut, vanilla, and caramel. Its unique aromatic profile contributes to enhancing the taste and aroma of food products, making it a valuable ingredient in the flavor industry.
Used in Cosmetics and Toiletries:
6-Methylcoumarin is used as a synthetic fragrance in cosmetics, toiletries, and soaps. Its pleasant scent adds a desirable aroma to these products, improving their overall appeal and consumer experience. 6-Methylcoumarin's stability and compatibility with various ingredients make it a popular choice for use in personal care products.

Preparation

6-methylcoumarin is synthesized from p-cresol and fumaric acid. Preheat 72% sulfuric acid to 80 °C, add a mixture of fumaric acid and p-cresol, keep the reaction at 160-170 °C for 3-4 hours, cool, pour into crushed ice to precipitate a precipitate, and filter. The filtrate was extracted with benzene, and after adding benzene, the obtained crude product was subjected to vacuum distillation to obtain 6-methylcoumarin. synthesis of 6-methylcoumarin: By heating 6-methyl coumarin-3-carboxylic acid to 300 to 340°C; by condensation of p-cresol-disulfonic acid with fumaric acid in the presence of H2SO4; by condensation of p-homosalicyclic aldehyde with malonic acid in the presence of aniline, followed by heating for the lactone; from salicylaldehyde with propionic acid anhydride and sodium propionate.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Ketones, such as 6-Methylcoumarin, are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Fire Hazard

6-Methylcoumarin is combustible.

Safety Profile

Poison by subcutaneous route. Moderately toxic by ingestion. A skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C10H8O2/c1-7-2-4-9-8(6-7)3-5-10(11)12-9/h2-6H,1H3

Upstream product

• 19063-55-9 6-bromo-2H-chromen-2-one 
• 74-88-4 methyl iodide 
• 10242-13-4 6-methyl-2-oxo-2H-chromene-3-carboxylic acid 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 108843-93-2 2,11-dimethyl-(6ar,6bt,12bt,12cc)-6a,6b,12b,12c-tetrahydro-cyclobuta[1,2-c;4,3-c'] dichromium ene-6,7-dione 
• 106-44-5 p-cresol 
• 110-16-7 maleic acid 
• 98712-54-0 4-hydroxy-toluene-3,5-disulfonic acid 
• 110-17-8 (2E)-but-2-enedioic acid 
• 77800-46-5 3t-[2]furyl-acrylic acid p-tolyl ester 
• 114106-33-1 3-(2-Hydroxy-5-methyl-phenyl)-3-(2-methoxycarbonyl-ethylsulfanyl)-propionic acid methyl ester 
• 115560-39-9 3-Hydroxy-3-(2-methoxymethoxy-5-methyl-phenyl)-N,N-dimethyl-propionamide 

Downstream Products

• 101110-20-7 6-methyl-4-phenylsulfanyl-chroman-2-one 
• 109089-21-6 6-methyl-4-p-tolylmercapto-chroman-2-one 
• 101596-93-4 4-benzylmercapto-6-methyl-chroman-2-one 
• 109092-90-2 6-methyl-4-o-tolylmercapto-chroman-2-one 
• 60257-28-5 2H-<1>benzopyran-2-thione 
• 92-47-7 3,4-dihydro-6-methyl-2H-1-benzopyran-2-one 
• 50396-43-5 2-hydroxy-5-methyl-cinnamic acid 
• 33538-75-9 3-(2-hydroxy-5-methylphenyl)propan-1-ol 
• 76510-25-3 3-(2-hydroxy-5-methyl-phenyl)-propionic acid 
• 51765-10-7 2-[(Z)-3-hydroxy-1-propenyl]-4-methylphenol 
• 86761-35-5 methyl (E)-3-(2′-methoxy-5′-methylphenyl)acrylate 
• 10242-09-8 5-methylbenzofuran-2-carboxylic acid 
• 4825-73-4 6-methyl-chroman-2,4-dione-4-oxime 
• 682804-15-5 3-amino-3-(2-hydroxy-5-methyl-phenyl)-propionic acid 

Relevant academic research and scientific papers

Dehydrogenative Carbon-Carbon Bond Formation Using Alkynyloxy Moieties as Hydrogen-Accepting Directing Groups

In the presence of a catalyst system consisting of Pd(OAc)2, PCy3, and Zn(OAc)2, the reaction of alkynyl aryl ethers with bicycloalkenes, α,ss-unsaturated esters, or heteroarenes results in the site-selective cleavage of two C-H bonds followed by the formation of C-C bonds. In all cases, the alkynyloxy group acts as a directing group for the activation of an ortho C-H bond and as a hydrogen acceptor, thus rendering the use of additives such as an oxidant or base unnecessary. Alkyne into alkene: A palladium catalyst enables dehydrogenative C-C bond-forming reactions between alkynyl aryl ethers and alkenes or heteroarenes. The presence of the alkynyloxy group is key for these transformations as it acts as a directing group for the site-selective cleavage of two C-H bonds as well as an acceptor for the released hydrogen.

Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2 H-Chromenes

Methods are reported for the efficient assembly of a series of phenol-derived propiolates, including the parent system 56, and their Au(I)-catalyzed cyclization (intramolecular hydroarylation) to give the corresponding coumarins (e.g., 1). Simple syntheses of natural products such as ayapin (144) and scoparone (145) have been realized by such means, and the first of these subject to single-crystal X-ray analysis. A related process is described for the conversion of propargyl ethers such as 156 into the isomeric 2H-chromene precocene I (159), a naturally occurring inhibitor of juvenile hormone biosynthesis.

Fe(III)-Catalyzed Decarboxylative C3-Difluoroarylmethylation of Coumarins with α,α-Difluoroarylacetic Acids

A facile Fe(III)-catalyzed oxidative decarboxylative radical coupling reaction of α,α-difluoroarylacetic acids with coumarins has been developed. This transformation, which provides a series of C-3 difluoroarylmethylated coumarins containing various functional groups in moderate-to-good yields, features easily accessible starting materials and operational simplicity.

Visible-light-induced regioselective alkylation of coumarins via decarboxylative coupling with N-hydroxyphthalimide esters

An efficient photocatalytic decarboxylative 3-position alkylation of coumarins by using alkyl N-hydroxyphthalimide esters as alkylation reagents has been developed. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) has been proved to be tolerated for this decarboxylation process, affording a broad scope of 3-alkylated coumarin derivatives in moderate to excellent yields. This protocol was highlighted by its mild conditions, readily available starting materials, operational simplicity, and wide functional group tolerance.

Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides

A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.

Synthesis method for coumarins compound

The invention discloses a synthesis method for a coumarins compound. The structural formula is shown in the specification, wherein R1 is selected from one or more of -H, -CH3, -OCH3, -F, -Cl, -Br, -OH, -NO2 and N(CH2CH3)2 and R2 is selected from one of -H, -CH3 or CH2CH3. According to the invention, a 2-hydroxy cinnamate compound is directly utilized as a raw material and the coumarins compound is synthesized in one step under the catalytic effect of visible light. Compared with the present synthesis method, the synthesis method for the coumarins compound disclosed by the invention has the characteristics of simple method, mild condition and high yield; the reaction is carried out under normal temperature; and the visible light is utilized as a reaction energy source and is green and pollution-free.

Bichromatic Photosynthesis of Coumarins by UV Filter-Enabled Olefin Metathesis

Herein, we report on a two-step bichromatic synthesis of coumarins involving UV-A and UV-C light. The first step is a UV-A-photoinduced ruthenium-catalyzed cross-metathesis (CM) reaction of 2-nitrobenzyl-protected 2-hydroxystyrenes with acrylates, using an external solution of 1-pyrenecarboxaldehyde as a UV filter. Irradiation in the absence of the filter permanently inhibits the light-activated catalyst due to photocleavage of the photolabile protecting group (PPG) and ensuing phenolate chelation to the ruthenium. The simple removal of the external filter after CM allows further photochemical reactions with UV-C light to achieve more complex architectures, such as the coumarins presented in this work. (Figure presented.).

Synthetic method of 6-methylcoumarin

The invention discloses a synthetic method of 6-methylcoumarin. The 6-methylcoumarin is synthesized through a one-step reaction of p-methyl phenol and ethyl formylacetate under the catalysis of phosphotungstic acid. Compared with the prior art, the method disclosed in the invention has the advantages of few synthesis steps and small environmental pollution.

Metal-free, Br?nsted acid-mediated synthesis of coumarin derivatives from phenols and propiolic acids

A novel synthesis of coumarin derivatives by Br?nsted acid-mediated condensation and intramolecular cyclization of phenols and propiolic acids was reported. This transformation requires the use of TfOH in place of a conventional metal mediator, and it occurs under mild conditions and provides rapid access to coumarin derivatives in good yields.

Process for preparing coumarin derivatives using phenol and propiolic acid

Provided is a manufacturing method of coumarin derivative. The manufacturing method of coumarin derivative comprises a step of making a phenol compound react with a propiolic acid compound. According to the present invention, the manufacturing method of coumarin derivative is quick and efficient, and is useful to fields requiring synthesis of coumarin derivatives of various structures.COPYRIGHT KIPO 2016