99179-39-2

Upstream product

• 59-47-2 mephenesin 
• 936-72-1 allyl o-tolyl ether 
• 6161-86-0 2-methylphenoxyethanol 
• 95-46-5 2-methylphenyl bromide 
• 95-48-7 ortho-cresol 
• 2210-79-9 o-Cresyl glycidyl ether 

Downstream Products

• 64899-61-2 4-o-tolyloxy-trans-crotonic acid 
• 91142-51-7 2-Hydroxy-1-(o-tolyloxy)-but-3-in 
• 94757-30-9 2,5-Dihydroxy-1,6-(o-tolyloxy)-hex-3-in 
• 134671-21-9 2C₁₀H₁₄N₄O₂*H₂O₄S 
• 74953-42-7 2-methylphenoxyacetaldehyde cyanohydrin 
• 103195-89-7 2-(o-tolyloxymethyl)thiazolidine 
• 95333-18-9 2-methylphenoxyacetaldehyde dimethyl acetal 
• 104730-53-2 (S)-2-methylphenoxyacetaldehyde cyanohydrin acetate 
• 119904-32-4 2-methylphenoxyacetaldehyde cyanohydrin acetate 
• 17059-52-8 7-methylbenzofuran 

Relevant academic research and scientific papers

Copper(ii)-catalyzed C-O coupling of aryl bromides with aliphatic diols: Synthesis of ethers, phenols, and benzo-fused cyclic ethers

A highly efficient copper-catalyzed C-O cross-coupling reaction between aryl bromides and aliphatic diols has been developed employing a cheaper, more efficient, and easily removable copper(ii) catalyst. A broad range of aryl bromides were coupled with aliphatic diols of different lengths using 5 mol% CuCl2 and 3 equivalents of K2CO3 in the absence of any other ligands or solvents to afford the corresponding hydroxyalkyl aryl ethers in good to excellent yields. In this newly developed protocol, aliphatic diols have multilateral functions as coupling reactants, ligands, and solvents. The resulting hydroxyalkyl aryl ethers were further readily converted into the corresponding phenols, presenting a valuable alternative way to phenols from aryl bromides. Furthermore, it was demonstrated that they are useful intermediates for more advanced molecules such as benzofurans and benzo-fused cyclic ethers. This journal is

Synthesis of aryloxyacetaldehydes and N-(aryloxyethyl)cyclohexanamine hydrochloroides

Oxidation of 2-(aryloxymethyl)oxiranes with periodic acid gave a series of aryloxyacetaldehydes which reacted with cyclohexylamine in THF, and subsequent reduction of Schiff bases thus obtained with sodium tetrahydridoborate resulted in the formation of the corresponding secondary amines which were isolated and characterized as hydrochlorides.

Ozonolysis of Olefins VIII [1]. Synthesis of Phenoxyacetaldehydes by Ozonolysis of Allylphenylethers

A new route for the preparation of a series of phenoxyacetaldehydes (2a-j) which are useful intermediates or products, is described. It starts from the easily available allylphenylethers 1a-j which are ozonized at -40°C and further treated with dimethylsulfide to give solutions of the corresponding phenoxyacetaldehydes 2a-j; these are purified by column chromatography. Reaction of 2a-j with 1-methyl-1-phenylhydrazine leads to the corresponding hydrazones 3a-c, 3e-g, 3i, and 3j. The aldehydes can also be transformed into the stable dimethylcetals 4a, 4e, 4h, and 4i by reaction with trimethyl orthoformate.

N-Acyl-2-substituted-1,3-thiazolidines, a New Class of Non-narcotic Antitussive Agents: Studies Leading to the Discovery of Ethyl 2--β-oxothiazolidine-3-propanoate

The synthesis of a novel class of antitussive agents is described.The compounds were examined for antitussive activity in guinea pig after cough induction by electrical or chemical stimulation.Ethyl 2--β-oxothiazolidine-3-propanoate (BBR 2173, moguisteine, 7) and other structurally related compounds showed a significant level of activity, comparable to that of codeine and dextromethorphan.The compounds presented in this paper are characterized by the N-acyl-2-substituted-1,3-thiazolidine moiety, which is a novel entry in the field of antitussive agents.The serendipitous discovery of the role played by the thiazolidine moiety in the determining the antitussive effect promoted extensive investigations on these structures.This optimization process on N-acyl-2-substituted-1,3-thiazolidines led to the initial identification of 2--3--1,3-thiazolidine (18a) as an interesting lead compound.The careful study of the rapid and very complicated metabolism of 18a provided further insights for the design of newer related derivatives.The observation that the metabolic oxidation on the lateral chain's sulfur of 18a to sulfoxide maintained the antitussive properties suggested the introduction of isosteric functional groups with respect to the sulfoxide moiety.Subsequent structural modifications showed that hydrolyzable malonic residues in the 3-position of the thiazolidine ring were able to assure high antitussive activity.This optimization ultimately led to the selection of moguisteine (7) as the most effective and safest representative of the series.Moguisteine is completely devoid of unwanted side effects (such as sedation and addiction), and its activity was demonstrated also in clinical studies.

Formation of Optically Active Aryloxyacetaldehyde Cyanohydrin Acetates with the Aid of a Microorganism

Microorganisms that hydrolyze the one enantiomer of dl-phenoxyacetaldehyde cyanohydrin acetate were screened, and Bacillus coagulans isolated from soil was found to be the best.This bacterium was applied to the asymmetric hydrolysis of other aryloxyacetaldehyde derivatives to give satisfactory results.The effect of adding dimethyl sulfoxide to the medium is also described.