30089-62-4

Usage

Class

Methoxybenzene derivatives

Psychoactive Drug

Yes

Hallucinogenic Effects

Yes

Structural Similarity

Mescaline

Benzene Ring

Present

Methoxy Groups

Two

Phenethylamine Moiety

Present

Controlled Substance

Yes, in many countries

Potential for Abuse

Yes

Recreational Use

Yes, for hallucinogenic effects

Side Effects

Can have harmful and potentially serious side effects

InChI:InChI=1/C16H18O2/c1-12(13-7-5-4-6-8-13)15-11-14(17-2)9-10-16(15)18-3/h4-12H,1-3H3

Upstream product

• 98-85-1 1-Phenylethanol 
• 150-78-7 1,4-dimethoxybezene 
• 100-42-5 styrene 
• 93-92-5 1-phenylethyl acetate 

Relevant academic research and scientific papers

Graphene-Catalyzed Direct Friedel-Crafts Alkylation Reactions: Mechanism, Selectivity, and Synthetic Utility

Transition-metal-catalyzed alkylation reactions of arenes have become a central transformation in organic synthesis. Herein, we report the first general strategy for alkylation of arenes with styrenes and alcohols catalyzed by carbon-based materials, exploiting the unique property of graphenes to produce valuable diarylalkane products in high yields and excellent regioselectivity. The protocol is characterized by a wide substrate scope and excellent functional group tolerance. Notably, this process constitutes the first general application of graphenes to promote direct C-C bond formation utilizing polar functional groups anchored on the GO surface, thus opening the door for an array of functional group alkylations using benign and readily available graphene materials. Mechanistic studies suggest that the reaction proceeds via a tandem catalysis mechanism in which both of the coupling partners are activated by interaction with the GO surface.

Cationic Iron(III) porphyrin catalyzed dehydrative friedel-crafts reaction of alcohols with arenes

Alcohols react with arenes in the presence of cationic iron(III) porphyrin catalyst. The reaction involves the formation of the C-C bond via dehydration, which is formal Lewis acid catalyzed Friedel-Crafts reaction. Georg Thieme Verlag Stuttgart, New York.

Microwave-accelerated alkylation of arenes/heteroarenes with benzylic alcohols using antimony(III) chloride as catalyst: Synthesis of O-heterocycles

An efficient protocol for alkylation of electron-rich arenes/heteroarenes with benzylic alcohols under microwave irradiation using antimony(III) chloride as catalyst has been developed. The mild reaction conditions, high yields, operational simplicity, and applicability to various substrates render the approach a useful route for the synthesis of diaryl/triarylalkane. In addition, a new route for the conversion of ortho-alkenylated phenols into functionalized O-heterocycles has been accomplished. Georg Thieme Verlag Stuttgart ? New York.

Process for the preparation of substituted phenols

A substituted phenolic compound is prepared by oxidizing a substituted diarylethane compound with oxygen in the presence of a nitrogen-containing cyclic compound, and treating the oxidized product with an acid. The nitrogen-containing cyclic compound includes, as a constituent of its ring, a skeleton represented by following Formula (I): wherein X is oxygen atom or an -OR group, where R is hydrogen atom or a hydroxyl-protecting group. The substituted diarylethane compound is represented by following Formula (1): wherein each of Ring Ar1 and Ring Ar2 is independently a monocyclic or polycyclic aromatic carbocyclic ring; Y1 is an electron-donating group; Y2 is an electron-withdrawing group; "p" is an integer of 1 or more; and "q" is an integer of 0 or more. The substituted phenolic compound is represented by following Formula (2): wherein Ring Ar1, Y1, and "p" are as defined above.

Highly efficient iodine-catalyzed hydroarylation of arenes with styrenes

Iodine mediates the hydroarylation of styrenes with arenes and heteroarenes to afford 1,1-diarylalkanes in good to high yields. Details regarding the substrate scope and selectivity of this hydroarylation reaction are discussed.

An effective bismuth-catalyzed benzylation of arenes and heteroarenes

A highly efficient Bi(OTf)3-catalyzed benzylation of arenes and heteroarenes has been developed. The mild reaction conditions, high yields, operational simplicity and practicability, broad scope, and remarkably low catalyst loading render this environment friendly process an attractive approach to diarylmethane derivatives. The extension to an intramolecular variant of this procedure provides a valuable route to substituted fluorenes.

An efficient and selective hydroarylation of styrenes with electron-rich arenes, catalyzed by bismuth(III) chloride and affording Markovnikov adducts

In the presence of BiCl3, the hydroarylation of styrenes with electron-rich arenes afforded Markovnikov adducts selectively in good to high yields. Under arene-free conditions, the intermolecular hydroarylation of α-substituted styrenes and subsequent intramolecular hydroarylation produced the cyclic dimers of α-substituted styrenes in good yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

A convenient FeCl3-catalyzed hydroarylation of styrenes

(Chemical Equation Presented) 1,1-Diarylalkanes are easily synthesized by CH-functionalization reactions of electron-rich arenes and heteroarenes with styrenes in the presence of FeCl3 as catalyst.

Gold-catalyzed benzylation of arenes and heteroarenes

Friedel-Crafts type benzylation of arenes and heteroarenes with benzylic acetates, alcohols, and carbonates is effectively promoted under mild reaction conditions using catalytic amounts of gold salts. The resulting 1,1-diarylalkanes and 1-aryl-1-heteroarylalkanes are obtained in high yields and with high selectivity. The utility of the method is demonstrated by a short synthesis of beclobrate {ethyl 2-[4-(4-chlorobenzyl)-phenoxy]-2-methylbutyrate (3)}, a fibric acid derivative.

Transition-metal-catalyzed benzylation of arenes and heteroarenes

Friedel-Crafts-type benzylation of various aromatic and heteroaromatic compounds with benzylic acetates, alcohols, and carbonates was promoted under mild reaction conditions by a series of Rh, Ir, Pd, and Pt catalysts (see scheme; R1 = H, Me; R2 = H, Cl, MeO; R3 = H, Ac, CO2Me). The desired products were obtained in high yields and with high selectivities.