Synthesis of Acid Hydrazides from Carboxylic Acids in Continuous Flow

Halloran, Matthew W.; Hudecek, Caitlin; Burkart, Michael D.

doi:10.1021/acs.oprd.3c00216

Title: Synthesis of Acid Hydrazides from Carboxylic Acids in Continuous Flow

Journal Article · 30 August 2023 · Organic Process Research & Development

DOI: https://doi.org/10.1021/acs.oprd.3c00216 · OSTI ID:2503942

^[1]; Hudecek, Caitlin ^[1];

^[1]

University of California San Diego, La Jolla, CA (United States)

A concise methodology for the synthesis of acid hydrazides from carboxylic acids via a continuous flow process in yields ranging from 65 to 91% is described. Using short residence times of between 13 and 25 mins, the conditions proved amenable to a variety of mono- and diacids, including aliphatic, aromatic, and heteroaromatic functionalities. Furthermore, to demonstrate scalability, a large-scale (200 g) synthesis of azelaic dihydrazide was conducted over a continuous run of 9 h with an 86% overall yield, equating to a 22 g/h output.

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Research Organization:: University of California San Diego, La Jolla, CA (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Office of Sustainable Transportation. Bioenergy Technologies Office (BETO)

Grant/Contract Number:: EE0009295

OSTI ID:: 2503942

Journal Information:: Organic Process Research & Development, Journal Name: Organic Process Research & Development Journal Issue: 9 Vol. 27; ISSN 1083-6160

Publisher:: ACS PublicationsCopyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
alcohols
carboxylic acid
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hydrazide
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organic reactions

Title: Synthesis of Acid Hydrazides from Carboxylic Acids in Continuous Flow

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