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Catechuic Acid and Ethyl 2,4,5-trihydroxybenzoate From D-glucose

Catechuic Acid and Ethyl 2,4,5-trihydroxybenzoate From D-glucose

Namdeo N Bhujbal, Omprakash P Bande, Dilip D Dhavale

Carbohydr Res. 2009 Apr 21;344(6):734-8.

PMID: 19268918

Abstract:

Synthesis of catechuic acid (1) and ethyl 2,4,5-trihydroxybenzoate (2) from D-glucose-derived beta-ketoester is described. The polyhydroxylated beta-ketoester obtained from the hydrolysis of sugar beta-ketoester 3 was subjected to an aldol-type condensation to get 4 that on enolization, dehydration, and hydrogenation afforded ethyl 2,4,5-trihydroxybenzoate (2). On the other hand, hydrogenation of aldol product 4 afforded polyhydroxylated keto-carbasugar 6, which on mild acid treatment and ester hydrolysis in basic media led to catechuic acid 1. Intermediate 4 is co-related to 3-dehydroshikimic acid, a biochemical intermediate from D-glucose in the synthesis of pro-catechuic acid.

Chemicals Related in the Paper:

Catalog Number	Product Name	CAS Number	Price
AP107099990	2,5-Dimethoxyphenylboronic acid	107099-99-0	Price
AP1072951611	4,5-Difluoro-2-isopropoxyphenylboronic acid	1072951-61-1	Price
AP150145258	2,4-Dipropoxyphenylboronic acid	150145-25-8	Price

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