95333-18-9

Upstream product

• 7252-83-7 1-bromo-2,2-dimethoxyethane 
• 95-48-7 ortho-cresol 
• 936-72-1 allyl o-tolyl ether 
• 99179-39-2 (2-methylphenoxy)acetaldehyde 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 90484-22-3 7-benzofuranylcarboxylic acid 
• 17059-52-8 7-methylbenzofuran 

Relevant academic research and scientific papers

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.

CONFORMATIONAL ANALYSIS OF ORGANIC CARBONYL COMPOUNDS. PART 4. A (1)H AND (13)C NUCLEAR MAGNETIC RESONANCE STUDY OF FORMYL AND ACETYL DERIVATIVES OF BENZOFURAN

A conformational study of formyl and acetyl derivatives of benzofuran provides evidence that in the case of 2- and 7-derivatives the E,Z-conformational mixture is solvent dependent, the Z-form prevailing in solvents with higher polarity.The presence of the same substituents in the 3- and 4-position gives compounds with predominantly Z-conformation and no change is caused by solvents.These results show an interestingly different behaviour by carbonyl derivatives of benzofuran with respect to the same benzothiophene derivatives.The conformational analysis was carried out by the n.m.r. method by employing (1)H and (13)C chemical shifts, long-range proton-proton coupling constants, and lanthanide-induced shifts (LIS) simulation.For the derivatives substituted in position 7, the LIS method is not a suitable approach for the determination of the conformer populations since, in solution, a chelate is formed where bonding of Eu to the oxygen atoms of the carbonyl and of the heterocyclic ring stabilizes the Z-form.A quantitative approach for determining the relative conformer populations of benzofuran-7-carbaldehyde was set up by statistical manipulation of long-range proton-proton coupling constants, proton chemical shifts, and the classical of dielectrics.