Influence of carboxylic acids on the synthesis of chlorohydrin esters from 1,3-butanediol

Jonh Jairo Méndez; Jordi Eras; Mercè Balcells; Ramon Canela

doi:10.1080/00397910500514055

Influence of carboxylic acids on the synthesis of chlorohydrin esters from 1,3-butanediol

Jonh Jairo Méndez, Jordi Eras, Mercè Balcells, Ramon Canela^*

^*Corresponding author for this work

Research output: Indexed journal article › Article › peer-review

7 Citations (Scopus)

Abstract

The influence of diverse carboxylic acid on the preparation of chlorohydrin esters using a one-pot esterification-chlorination reaction, in which one of the reagents (chlorotrimethylsilane) acts as solvent, is described. Whereas the acid with low pKa provided higher amounts of the 2-chloro regioisomer, the ones with higher pKa rendered the 1-chloro regioisomer in 80% yield. These results are in accordance with the mechanism proposed in a previous article.

Original language	English
Pages (from-to)	1167-1175
Number of pages	9
Journal	Synthetic Communications
Volume	36
Issue number	9
DOIs	https://doi.org/10.1080/00397910500514055
Publication status	Published - 2006
Externally published	Yes

Keywords

Carboxylic acids
Chlorohydrin esters
Chlorotrimethylsilane
Diol
Halogenation
Regioselectivity

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10.1080/00397910500514055

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title = "Influence of carboxylic acids on the synthesis of chlorohydrin esters from 1,3-butanediol",

abstract = "The influence of diverse carboxylic acid on the preparation of chlorohydrin esters using a one-pot esterification-chlorination reaction, in which one of the reagents (chlorotrimethylsilane) acts as solvent, is described. Whereas the acid with low pKa provided higher amounts of the 2-chloro regioisomer, the ones with higher pKa rendered the 1-chloro regioisomer in 80% yield. These results are in accordance with the mechanism proposed in a previous article.",

keywords = "Carboxylic acids, Chlorohydrin esters, Chlorotrimethylsilane, Diol, Halogenation, Regioselectivity",

author = "M{\'e}ndez, {Jonh Jairo} and Jordi Eras and Merc{\`e} Balcells and Ramon Canela",

year = "2006",

doi = "10.1080/00397910500514055",

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T1 - Influence of carboxylic acids on the synthesis of chlorohydrin esters from 1,3-butanediol

AU - Méndez, Jonh Jairo

AU - Eras, Jordi

AU - Balcells, Mercè

AU - Canela, Ramon

PY - 2006

Y1 - 2006

N2 - The influence of diverse carboxylic acid on the preparation of chlorohydrin esters using a one-pot esterification-chlorination reaction, in which one of the reagents (chlorotrimethylsilane) acts as solvent, is described. Whereas the acid with low pKa provided higher amounts of the 2-chloro regioisomer, the ones with higher pKa rendered the 1-chloro regioisomer in 80% yield. These results are in accordance with the mechanism proposed in a previous article.

AB - The influence of diverse carboxylic acid on the preparation of chlorohydrin esters using a one-pot esterification-chlorination reaction, in which one of the reagents (chlorotrimethylsilane) acts as solvent, is described. Whereas the acid with low pKa provided higher amounts of the 2-chloro regioisomer, the ones with higher pKa rendered the 1-chloro regioisomer in 80% yield. These results are in accordance with the mechanism proposed in a previous article.

KW - Carboxylic acids

KW - Chlorohydrin esters

KW - Chlorotrimethylsilane

KW - Diol

KW - Halogenation

KW - Regioselectivity

UR - http://www.scopus.com/inward/record.url?scp=33645284435&partnerID=8YFLogxK

U2 - 10.1080/00397910500514055

DO - 10.1080/00397910500514055

M3 - Article

AN - SCOPUS:33645284435

SN - 0039-7911

VL - 36

SP - 1167

EP - 1175

JO - Synthetic Communications

JF - Synthetic Communications

IS - 9

ER -

Influence of carboxylic acids on the synthesis of chlorohydrin esters from 1,3-butanediol

Abstract

Keywords

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