20920-83-6

Usage

InChI:InChI=1/C9H12O2/c1-2-11-7-8-5-3-4-6-9(8)10/h3-6,10H,2,7H2,1H3

Upstream product

• 80171-91-1 2-ethoxymethyl-aniline 
• 90-02-8 salicylaldehyde 
• 79411-60-2 l'α-chloro α-ethoxymethyltributyletain 
• 64-17-5 ethanol 
• 18885-85-3 2-phenyl-4H-benzo-1,3,2-dioxaborine 
• 5122-82-7 1-adamantyl bromomethyl ketone 
• 39487-54-2 1-((dimethylamino)(phenyl)methyl)naphthalen-2-ol 
• 17760-81-5 1-[2-oxo-2-(tricyclo[3.3.1.1^3,7]dec-1-yl)ethyl]pyridinium bromide 
• 612-23-7 2-nitrobenzyl chloride 
• 66424-93-9 2-ethoxymethyl-1-nitrobenzene 
• 94-67-7 salicylaldehyde-oxime 
• 932-30-9 2-Hydroxybenzylamine 
• 89-95-2 2-methyl-benzyl alcohol 
• 132980-32-6 2-(1H-1,2,3-benzotriazol-1-ylmethyl)phenol 

Downstream Products

• 330976-42-6 phosphorochloridite 

Relevant academic research and scientific papers

Zinc-mediated reactions on salicylaldehyde for Botrytis cinerea control

Botrytis cinerea is a necrotrophic fungus that affects various plant species. Chemical control is a necessity and as much as possible, eco-friendly conditions and bioresources to obtain these chemicals should be used. In this context, a series of products was obtained from salicylaldehyde using zinc as a powerful reagent and tested for antifungal activity against Botrytis cinerea

Reactions of O-quinone methides with pyridinium methylides: A diastereoselective synthesis of 1,2-dihydronaphtho[2,1- b ]furans and 2,3-dihydrobenzofurans

A simple, general route to the 1,2-dihydronaphtho[2,1-b]furans and 2,3-dihydrobenzofurans substituted at C-2 by an acyl or aryl group, starting from phenolic Mannich bases and pyridinium ylides, has been developed. The mechanism of the reaction is believed to involve the formation of the o-quinone methide intermediate, Michael-type addition of the ylide to the o-quinone methide, followed by intramolecular nucleophilic substitution.

Hydroxy-1-aminoindans and derivatives: Preparation, stability, and reactivity

The chemical stability and reactivity of hydroxy-1-aminoindans and their N-propargyl derivatives are strongly affected by the position of the OH group and its orientation relative to that of the amino moiety. Thus, the 4- and 6-OH regioisomers were found to be stable, while the 5-OH analogues were found to be inherently unstable as the free bases. The latter, having a para orientation between the OH and the amino moieties, could be isolated only as their hydrochloride salts. 7-Hydroxy-1-aminoindans and 7-hydroxy-1- propargylaminoindans represent an intermediate case; while sufficiently stable even as free bases, they exhibit, under certain experimental conditions, unexpected reactivity. The instability of the 5- and 7-hydroxy-aminoindans is attributed to their facile conversion to the corresponding, reactive quinone methide (QM) intermediates. The o-QM obtained from 7-hydroxy-aminoindans was successfully trapped with ethyl vinyl ether via a Diels-Alder reaction to give tricyclic acetals 32a,b.

Reductive etherification of aromatic aldehydes with decaborane

Aromatic aldehydes were easily convened to the corresponding ethers in methanol or ethanol using decaborane at r.t. under nitrogen in high yields.

The reactivity of o-hydroxybenzyl alcohol and derivatives in solution at elevated temperatures

The reactivity of o-hydroxybenzyl alcohol (o-HBA, 1), as a model compound for lignin, has been studied in various solvents between 390 and 560 K. Both in polar and apolar solvents the benzylic cation is the reactive intermediate. In alcoholic solvents, the benzylic cation reacts with the solvent to give the corresponding ethers. Relative reaction rates have been determined for different alcohols; a factor of 14 is encountered between the most (methanol) and least (tert-butyl alcohol) reactive ones. The etherification is reversible, in contrast to the electrophilic aromatic substitution with phenol and anisole, for which k(PhOH) = 1 X 105 M-1 s- 1 and k(anisole) = 1 x 104 M-1 s-1, at 424 K. In apolar hydroaromatic solvents, 7H-benz[de]anthracene, 9,10-dihydroanthracene, and 9,10- dihydrophenanthrene, the formation of o-cresol proceeds via hydride transfer from the solvent to the benzylic cation; rate constants at 555 K are 2 x 106, 5 x 104, and 5 x 103 M-1 s-1, respectively.

ortho-Specific alkylation of phenols via 1,3,2-benzodioxaborins

Reaction of a phenol with an aldehyde in the presence of phenylboronic acid gives a 1,3,2-benzodioxaborin.The latter could be reduced to the corresponding ortho-alkylphenol with tert-butylamine borane in the presence of aluminum chloride.Alternatively, the dioxaborin, when reacted with an alkylthiol or an alcohol in the presence of an acid, gave the corresponding ortho-alkylthiomethyl- or ortho-alkoxymethylphenol.Key words: phenol, alkylation, ortho-specific, 1,3,2-benzodioxaborin.

QUELQUES ASPECTS DE LA REACTIVITE DE L'α-CHLORO α-ETHOXYMETHYLTRIBUTYLETAIN: ETHERIFICATION REDUCTRICE DES ALDEHYDES AROMATIQUES ET MISE EN EVIDENCE DE FORMYLTRIBUTYLETAIN LORS DE LA REACTION D'HYDROLYSE

α-Chloro-α-ethoxymethyltributyltin reacts with aromatic aldehydes and leads to benzyl ethyl ethers with formation of tributyltin chloride and carbon monoxide.Analogously the formation of ethoxymethyltributyltin and tributyltyn chloride on hydrolysis of this new organometallic reagent is explained by a process involving formyltributyltin as an unstable intermediate.This explanation is supported by the observation of an electronic spectrum between 350 and 450 nm during the hydrolysis.