24258-63-7

Usage

Preparation

Preparation by Fries rearrangement of p-cresyl phenylacetate with aluminium chloride (68%), ? without solvent at 120–140° for 20 min (82%) , at 130–135° for 30 min (80%) or at 130–140° for 3 h (14%); ? in nitrobenzene at r.t. for 48 h (80%) or at 60° for 4 h (64%) ; ? in 1,2,4-trichlorobenzene at reflux for 30 min (78%); ? in chlorobenzene at reflux for 4 h (23%) or for 30 min (86%).

Upstream product

• 103-82-2 phenylacetic acid 
• 106-44-5 p-cresol 
• 101-94-0 p-tolyl phenylacetate 
• 104-93-8 p-methylanizole 
• 103-80-0 phenylacetyl chloride 
• 7446-70-0 aluminium trichloride 

Downstream Products

• 10366-16-2 4-methyl-2-phenethylphenol 
• 70978-50-6 4-Methyl-6-nitro-2-phenylacetylphenol 
• 119304-60-8 1-(2-Hydroxy-5-methyl-phenyl)-2-phenyl-3-pyrrolidin-1-yl-propan-1-one 
• 63136-70-9 5-methyl-2-phenyl-3(2H)-benzofuranone 
• 100733-58-2 Benzyloxy-thiocarbonyl-hydrazon des 2-Hydroxy-5-methyl-phenyl-benzylketons 
• 1217-93-2 6-methyl-3-phenyl-4H-chromen-4-one 
• 132593-82-9 4-acetoxy-6-methyl-3-phenyl-coumarin 
• 70977-87-6 6-Amino-4-methyl-2-phenylacetyl-phenol 
• 70978-00-6 1-(4-methoxy-benzyl)-1H-tetrazole-5-carboxylic acid 2-hydroxy-5-methyl-3-phenylacetyl-anilide 
• 70977-65-0 1⁽²⁾H-tetrazole-5-carboxylic acid 2-hydroxy-5-methyl-3-phenylacetyl-anilide 
• 25871-52-7 5-methyl-2-phenylbenzofuran 

Relevant academic research and scientific papers

Synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarinviaa TsOH-mediated tandem reaction

A concise and efficient method for the synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarin using available 1-(2-hydroxyphenyl)-2-phenylethanone and Meldrum's acid has been developed. This transformation involved a tandem aldol reaction/lactonization/Friedel-Crafts reaction to form a lactone ring and a benzene ring. It showed high atom economy with water and acetone as the byproducts. Mechanism studies demonstrated two roles of Meldrum's acid: (i) as the reagent for the tandem reaction, and (ii) as the catalyst for the Friedel-Crafts reaction. Moreover, the hydroxyl group of 7-hydroxy-6H-naphtho[2,3-c]coumarin was further functionalized efficiently by arylethynyl, aryl, and cyano groups to furnish D-π-A compounds with excellent fluorescence emissions (ΦF= 0.14-0.78).

C-H Functionalization via Remote Hydride Elimination: Palladium Catalyzed Dehydrogenation of ortho-Acyl Phenols to Flavonoids

Although deprotonation of electron-poor C-H bonds to carbon anions with bases has long been known and widely used in organic synthesis, the hydride elimination from electron-rich C-H bonds to carbon cations or partial carbocations for the introduction of nucleophiles is a comparatively less explored area. Here we report that the carbonyl β-C(sp3)-H bond hydrogens of ortho-acyl phenols could be substituted by intramolecular phenolic hydroxyls to form O-heterocycles, followed by dehydrogenation of the O-heterocycle into flavonoids. The cascade reaction is catalyzed by Pd/C without added oxidants and sacrificing hydrogen acceptors.

Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging

Starting from 7-hydroxyisoflavones, we developed a new class of fluorescent scaffolds, 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs, MW ～ 205.19, λab ～ 350 nm, λem ～ 450 nm) via a trial and error process. AMHCs have the advantages of being a small molecular moiety, having strong fluorescence in basic buffers, reasonable solubility and stability, non-toxicity, and are conveniently linked to pharmacophores. AMHCs were successfully used in fluorescence microscopy imaging of cells and tissues. This journal is

An improved synthesis of hydroxy aryl ketones by fries rearrangement with methanesulfonic acid/methanesulfonic anhydride

Methanesulfonic acid treated with methanesulfonic anhydride effectively mediates the Fries rearrangement of aryl esters to give hydroxy aryl ketones with high yields. Georg Thieme Verlag Stuttgart · New York.

The Mannich Reaction of 1-(2-Hydroxyphenyl)-1-ethanone, -1-propanone and -1-butanone, and 1-(2-Hydroxy-5-methylphenyl)-2-phenyl-1-ethanone

The title compounds on reaction with secondary amines in the presence of formaldehyde under acidic condition, gave the corresponding Mannich bases by ω-aminomethylation.