Systematic Evaluation of Sulfoxides as Catalysts in Nucleophilic Substitutions of Alcohols was written by Motsch, Sebastian;Schuetz, Christian;Huy, Peter H.. And the article was included in European Journal of Organic Chemistry in 2018.Safety of Methyl 2-chloro-2-phenylacetate This article mentions the following:
Herein, a method for the nucleophilic substitution (SN) of benzyl alcs. yielding chloro alkanes is introduced that relies on aromatic sulfoxides as Lewis base catalysts (down to 1.5 mol-%) and benzoyl chloride (BzCl) as reagent. A systematic screening of various sulfoxides and other sulfinyl containing Lewis bases afforded (2-methoxyphenyl)methyl sulfoxide as optimal catalyst. In contrast to reported formamide catalysts, sulfoxides also enable the application of plain acetyl chloride (AcCl) as reagent. In addition, it was demonstrated that weakly electrophilic carboxylic acid chlorides like BzCl promote Pummerer rearrangement of sulfoxides already at room temperature This side-reaction also provided the explanation, why sulfoxide catalyzed SN-reactions of alcs. do not allow the effective production of aliphatic and electron deficient chloro alkanes. Comparison experiments provided further insight into the reaction mechanism. In the experiment, the researchers used many compounds, for example, Methyl 2-chloro-2-phenylacetate (cas: 7476-66-6Safety of Methyl 2-chloro-2-phenylacetate).
Methyl 2-chloro-2-phenylacetate (cas: 7476-66-6) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications. Organochlorine compounds are lipophylic, meaning they are more soluble in fat than in water. This gives them a high tenancy to accumulate in the food chain (biomagnification).Safety of Methyl 2-chloro-2-phenylacetate
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics