Electrochemical Mediated Esterification Reaction of Carboxylic Acids and Alcohols

doi:10.6023/cjoc202302004

Abstract

A series of esters were prepared by electrochemical synthesis of carboxylic acids with alcohols. This protocol can be carried out at room temperature without inert atmosphere, strong acids or metal catalysts, etc. The esterification reaction processes in an undivided electrolytic cell with constant current mode and the esterification products are generated in good yields. Compared with esterification promoted by organic reagents, this protocol avoids the byproducts which have to be separated by column chromatography and successful for tertiary alcohol which is generally difficult to undergo esterification directly, providing a new access to the esterification of carboxylic acids and alcohols.

Key words: electrochemical mediation, esterification reaction, electromechanical synthesis

Cite this article

Yunzhe Zhong, Ying hen, Lei Yu, Hongwei Zhou. Electrochemical Mediated Esterification Reaction of Carboxylic Acids and Alcohols[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2855-2863.

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Entry	Additive	Solvent	Current/mA	Electrode	Yield^b/%
1^c	TBAB/Na₂S₂O₅	EtOH	5	Graphite (＋)/Pt(－)	54
2^d	TBAB/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	86
3^e	TBAB/Na₂S₂O₅	EtOH	15	Graphite (＋)/Pt(－)	84
4	KBr/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	25
5	KCl/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	NR
6	TBAB/Na₂S₂O₅	CH₃CN	10	Graphite (＋)/Pt(－)	56
7	TBAB/Na₂S₂O₅	DMF	10	Graphite (＋)/Pt(－)	47
8	TBAB/Na₂S₂O₅	DCE	10	Graphite (＋)/Pt(－)	37
9	TBAB/Na₂S₂O₅	Acetone	10	Graphite (＋)/Pt(－)	83
10	TBAB/Na₂S₂O₅	EtOH	10	Graphite (＋)/Graphite (－)	48
11	TBAB/Na₂S₂O₅	EtOH	10	Glassy carbon (＋)/Pt(－)	62
12	TBAB/Na₂S₂O₅	EtOH	10	Pt (＋)/Pt(－)	NR
13^f	TBAB/Na₂S₂O₅	EtOH	—	Graphite (＋)/Pt(－)	NR
14^g	TBAB	EtOH	10	Graphite (＋)/Pt(－)	NR
15^h	TBAB/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	76

Entry	Additive	Solvent	Current/mA	Electrode	Yield^b/%
1^c	TBAB/Na₂S₂O₅	EtOH	5	Graphite (＋)/Pt(－)	54
2^d	TBAB/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	86
3^e	TBAB/Na₂S₂O₅	EtOH	15	Graphite (＋)/Pt(－)	84
4	KBr/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	25
5	KCl/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	NR
6	TBAB/Na₂S₂O₅	CH₃CN	10	Graphite (＋)/Pt(－)	56
7	TBAB/Na₂S₂O₅	DMF	10	Graphite (＋)/Pt(－)	47
8	TBAB/Na₂S₂O₅	DCE	10	Graphite (＋)/Pt(－)	37
9	TBAB/Na₂S₂O₅	Acetone	10	Graphite (＋)/Pt(－)	83
10	TBAB/Na₂S₂O₅	EtOH	10	Graphite (＋)/Graphite (－)	48
11	TBAB/Na₂S₂O₅	EtOH	10	Glassy carbon (＋)/Pt(－)	62
12	TBAB/Na₂S₂O₅	EtOH	10	Pt (＋)/Pt(－)	NR
13^f	TBAB/Na₂S₂O₅	EtOH	—	Graphite (＋)/Pt(－)	NR
14^g	TBAB	EtOH	10	Graphite (＋)/Pt(－)	NR
15^h	TBAB/Na₂S₂O₅	EtOH	10	Graphite (＋)/Pt(－)	76

电化学介导羧酸与醇的酯化反应