433331-88-5

Upstream product

• 150-19-6 O-methylresorcine 
• 123-11-5 4-methoxy-benzaldehyde 
• 1160046-95-6 1-((3-methoxyphenoxy)methyl)-4-methoxybenzene 
• 824-94-2 p-methoxybenzyl chloride 
• 433331-87-4 2-hydroxy-4,4'-dimethoxydiphenylmethanol 

Downstream Products

• 679410-96-9 4-[5-methoxy-2-(4-methoxybenzyl)phenoxy]phenol 

Relevant academic research and scientific papers

Experimental and Computational Studies on the Ruthenium-Catalyzed Dehydrative C-H Coupling of Phenols with Aldehydes for the Synthesis of 2-Alkylphenol, Benzofuran, and Xanthene Derivatives

The cationic Ru-H complex [(C6H6)(PCy3)(CO)RuH]+BF4- (1) was found to be an effective catalyst for the dehydrative C-H coupling reaction of phenols and aldehydes to form 2-alkylphenol products. The coupling reaction of phenols with branched aldehydes selectively formed 1,1-disubstituted benzofurans, while the coupling reaction with salicylaldehydes yielded xanthene derivatives. A normal deuterium isotope effect was observed from the coupling reaction of 3-methoxyphenol with benzaldehyde and 2-propanol/2-propanol-d8 (kH/kD = 2.3 ± 0.3). The carbon isotope effect was observed on the benzylic carbon of the alkylation product from the coupling reaction of 3-methoxyphenol with 4-methoxybenzaldehyde (C(3) 1.021(3)) and on both benzylic and ortho-arene carbons from the coupling reaction with 4-trifluorobenzaldehdye (C(2) 1.017(3), C(3) 1.011(2)). The Hammett plot from the coupling reaction of 3-methoxyphenol with para-substituted benzaldehydes p-X-C6H4CHO (X = OMe, Me, H, F, Cl, CF3) displayed a V-shaped linear slope. Catalytically relevant Ru-H complexes were observed by NMR from a stoichiometric reaction mixture of 1, 3-methoxyphenol, benzaldehyde, and 2-propanol in CD2Cl2. The DFT calculations provided a detailed catalysis mechanism featuring an electrophilic aromatic substitution of the aldehyde followed by the hydrogenolysis of the hydroxy group. The calculations also revealed a mechanistic rationale for the strong electronic effect of the benzaldehdye substrates p-X-C6H4CHO (X = OMe, CF3) in controlling the turnover-limiting step. The catalytic C-H coupling method provides an efficient synthetic protocol for 2-alkylphenols, 1,1-disubstituted benzofurans, and xanthene derivatives without employing any reactive reagents or forming wasteful byproducts.

Conversion of substituted benzyl ethers to diarylmethanes. A direct synthesis of diarylbenzofurans

The Lewis acid catalyzed rearrangement of substituted benzyl ethers affords diarylmethanes in good yields. One of the products was converted into a diarylbenzofuran using a benzoylation/P4-tBu cyclization protocol.

Synthetically useful Bronsted acid-promoted arylbenzyl ether → o-benzylphenol rearrangements

(Chemical Equation Presented) Camphorsulfonic acid in warm fluorobenzene facilitates the ortho rearrangement of (alkoxy-substituted) benzyl ethers of 1-(O-methyl)-2-nitroresorcinols to the corresponding o-(alkoxy-substituted) arylmethylnitrophenols. The s

Efficient preparation and processing of the 4-methoxybenzyl (PMB) group for phenolic protection using ultrasound

(Chemical Equation Presented) Power ultrasound efficiently facilitates the rapid preparation and reaction of 4-methoxybenzyl chloride (PMB-Cl) 1 in providing protected phenolic ether intermediates for organic synthesis. Using two-phase systems in both the ultrasound-promoted preparation and reactions of PMB-Cl, typical runs produce PMB-protected products within 15 min. When compared with nonsonicated control reactions, the results demonstrate clear advantage in terms of efficiency when the protocol is applied to the mild and selective protection of various multisubstituted phenols including sensitive phenolic aldehydes.

GLUCOPYRANOSYLOXYBENZYLBENZENE DERIVATIVES AND MEDICINAL USE THEREOF

The present invention provides glucopyranosyloxybenzylbenzene derivatives represented by the general formula: wherein P represents a hydrogen atom or a group forming a prodrug; R1 represents a hydrogen atom, an optionally substituted amino grou

GLUCOPYRANOSYLOXYBENZYL BENZENE DERIVATIVES, MEDICINAL COMPOSITIONS CONTAINING THE SAME AND INTERMEDIATES IN THE PRODUCTION THEREOF

The present invention relates to glucopyranosyloxybenzylbenzene derivatives represented by the general formula: wherein R1 represents a hydrogen atom, a hydroxy group, a substituted or unsubstituted amino group, a carbamoyl group, a substituted or unsubstituted(lower alkyl) group, a substituted or unsubstituted(lower alkoxy) group etc.; R2 represents a hydrogen atom or a lower alkyl group; and R3 represents a substituted or unsubstituted(lower alkyl) group, a substituted or unsubstituted(lower alkoxy) group, a substituted or unsubstituted (lower alkylthio) group etc., or pharmaceutically acceptable salts thereof, which have an inhibitory activity in human SGLT2 and are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, diabetic complication or obesity, pharmaceutical compositions comprising the same and intermediates thereof.