Role of the peri-effect in synthesis and reactivity of highly substituted naphthaldehydes: a novel backbone amide linker for solid-phase synthesis was written by Pittelkow, Michael;Boas, Ulrik;Jessing, Mikkel;Jensen, Knud J.;Christensen, Jorn B.. And the article was included in Organic & Biomolecular Chemistry in 2005.HPLC of Formula: 6834-42-0 This article mentions the following:
This work describes the design, synthesis and properties of a novel trialkoxynaphthalene-based backbone amide linker (NAL-3). The NAL-3 handle is based on a trialkoxynaphthaldehyde (NALdehyde-3) that was synthesized in nine high-yielding steps from 3-methoxyphenylacetic acid in 51% overall yield. The naphthalene ring system was constructed using a regioselective methanesulfonic acid-catalyzed ring-closing reaction. The tetra-substituted naphthalene derivative 1,3,6-trimethoxynaphthalene-2-carbaldehyde was selectively demethylated in the 1 position using BBr3. The selectivity of this reaction is discussed, based on the crystal structures of above reactant and product, 1-hydroxy-3,6-dimethoxy-naphthalene-2-carbaldehyde, and in the context of the peri-effect. The new handle was anchored to an aminomethylated poly(styrene) solid support, followed by assembly of a model dipeptide, then a study of the cleavage properties under acidic conditions was carried out. Surprisingly, the trialkoxynaphthaldehyde-based handle proved less acid-labile than the dialkoxynaphthaldehyde handles, and this fact is discussed with respect to handle design. In the experiment, the researchers used many compounds, for example, 2-(3-Methoxyphenyl)acetyl chloride (cas: 6834-42-0HPLC of Formula: 6834-42-0).
2-(3-Methoxyphenyl)acetyl chloride (cas: 6834-42-0) belongs to organic chlorides. Chlorinated organic compounds are found in nearly every class of biomolecules and natural products including alkaloids, terpenes, amino acids, flavonoids, steroids, and fatty acids. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.HPLC of Formula: 6834-42-0
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics