Synthesis of carboxylic acids, esters and their

derivatives

THE CHEMISTRY OF FUNCTIONAL GROUPS

A series ofadvanced treatises under the general editorship of Professor Saul Patai

The chemistry of alkenes (2 volumes) The chemistry of the carbonyl group (2 volumes)

The chemistry of the ether linkage The chemistry of the amino group

The chemistry of the nitro and nitroso groups (2 parts) The chemistry of carboxylic acids and esters

The chemistry of the carbon-nitrogen double bond The chemistry of amides

The chemistry of the cyano group The chemistry of the hydroxyl group (2 parts)

The chemistry of the azido group The chemistry of acyl halides

The chemistry of the carbon-halogen bond (2 parts) The chemistry of the quinonoid compounds (2 volumes 4 parts)

The chemistry of the thiol group (2 parts) The chemistry of the hydrazo azo and azoxy groups (2 parts)

The chemistry of amidines and imidates (2 volumes) The chemistry of cyanates and their thio derivatives (2 parts)

The chemistry of diazonium and diazo groups (2 parts) The chemistry of the carbon-carbon triple bond (2 parts)

The chemistry of ketenes, allenes and related compounds (2 parts) The chemistry of the sulphonium group (2 parts)

Supplement A The chemistry of double-bonded functional groups (2 volumes 4 parts) Supplement B The chemistry of acid derivatives (2 parts)

Supplement C The chemistry of triple-bonded functional groups (2 parts) Supplement D The chemistry of halides, pseudo-halides and azides (2 parts)

Supplement E The chemistry of ethers crown ethers hydroxyl groups and their sulphur analogues (2 parts)

Supplement F The chemistry of amino, nitroso and nitro compounds and their derivatives (2 parts)

The chemistry of the metal-carbon bond (5 volumes) The chemistry of peroxides

The chemistry of organic selenium and tellurium compounds (2 volumes) The chemistry of the cyclopropyl group

The chemistry of organic silicon compounds (2 parts) The chemistry of enones (2 parts)

The chemistry of sulphinic acids esters and their derivatives The chemistry of sulphenic acids and their derivatives

The chemistry of organophosphorus compounds The chemistry of enols

The chemistry of sulphonic acids esters and their derivatives

UPDATES The chemistry of a-haloketones a-haloaldehydes and a haloimines

Nitrones nitronates and nitroxides Crown ethers and analogs

Cyclopropane derived reactive intermediates Synthesis of carboxylic acids esters and their derivatives

Patai s guide to the chemistry of functional groups-Saul Para/

Synthesis of carboxylic acids, esters and their derivatives

MICHAEL A. OGLIARUSO

and

JAMES F. WOLFE

Virginia Polytechnic Institute and State University

Edited by

SAUL PATAI and ZVI RAPPOPORT

The Hebrew University of Jerusalem

Updates from the Chemistry of Functional Groups

1991

JOHN WILEY & SONS

CHICHESTER . NEW YORK . BRISBANE . TORONTO. SINGAPORE

An Intersciences Publication

Copyright 0 1991 by John Wiley & Sons Ltd Baffins Lane, Chichester, West Sussex PO19 IUD, England

All rights reserved

No part of this book may be reproduced by any means, or transmitted, or translated into a machine language without the written permission of the publisher

Other Wiley Editorial Offices

John Wiley & Sons, Inc., 605 Third Avenue, New York, NY 10158-0012, USA

Jacaranda Wiley Ltd, G.P.O. Box 859, Brisbane, Queensland 4001, Australia

John Wiley & Sons (Canada) Ltd, 22 Worcester Road, Rexdale, Ontario M9W 1L1, Canada

John Wiley & Sons (SEA) Pte Ltd, 37 Jalan Pemimpin 05-04, Block B, Union Industrial Building, Singapore 2057

Library of Congress Cataloging-in-Publication Data:

Wolfe, James F. Synthesis of carboxylic acids, esters, and their derivatives / by

Michael A. Ogliaruso, James F. Wolfe Rappoport.

; edited by Saul Patai and Zvi

p. cm.-(The Chemistry of functional groups) ‘An Interscience publication.’ Includes bibliographical references and index. ISBNO 471 91717 6 I. Carboxylic acids. 2. Esters. 3. Organic compounds-Synthesis.

I. Wolfe, James F. 11. Patai, Saul. 111. Rappoport, Zvi. IV. Title. V. Series. QD305A2W84 1991 90-43886 547‘.037-d~20 CIP

British Library Cataloguing in Publication Data:

Ogliaruso, Michael A. Synthesis of carboxylic acids, esters and their derivatives. 1. Carboxylic acids. Derivatives 1. Title 11. Wolfe, James F. 111. Patai, Saul IV. Rappoport, Zvi V. Series 547.037

2. Esters. Derivatives

ISBNO 471 91717 6

Typeset by Thomson Press (India) Ltd, New Delhi, India. Printed in Great Britain by Courier International Ltd, Tiptree, Essex

List of contributors

M. A. Ogliaruso

J. F. Wolfe

Department of Chemistry, College of Arts and Sciences, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061 -0699, USA

Department of Chemistry, College of Arts and Sciences, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061-0699, USA

V

This is the fifth volume in the new series entitled ‘Updates from the Chemistry of Functional Groups’.

The volume contains the chapter by Professors M. A. Ogliaruso and J. F. Wolfe entitled ‘The synthesis ofcarboxylic acids and esters and their derivatives’as it appeared in 1979 in ‘Supplement B. The chemistry ofacid derivatives’. It is typical of the rapid development of this subject that the ‘Appendix’ written by the same authors is almost twice as large as the original chapter, although only a decade passed between the preparation of the two.

We will appreciate comments and suggestions regarding the present volume as bell as other volumes of the main series or their updates.

Jerusalem January 1991

SAUL PATAI ZVI RAPPOPORT

vii

Preface

Carboxylic acids, esters and their derivatives occupy a central position in the chemistry of naturally occurring and synthetic organic compounds. Consequently, methods for the synthesis and interconversions of these functional groups are of prime importance to essentially every practicing organic chemist at one time or another. In view of this, and in order to provide the series, The chemistry of Functional Groups, with a single source of information on general methods for the synthesis of carboxylic acids, esters, acid anhydrides, acyl halides, amides and imides, we authored a chapter on the synthesis of carboxylic acids and their derivatives, which appeared in Suppkment B: The chemistry of acid deriwtives. Purr I , pp. 267-490. That chapter contained descriptions of the most common methods for the synthesis of acids and acid derivatives, with emphasis on preparative techniques that appeared in the primary literature during the period, I967 through early 1976.

The present monograph volume on the synthesis of carboxylic acids and acid derivatives represents our response to an invitation by the Editors and publishers of the ‘Functional Groups’ series of books to combine the material contained in the original chapter with new methodology from the literature for the period, 1976 through 1987. The format for this combination consists ofthe original text as published in 1979, along with an up-to-date Appendix containing the newer material in the same format as used earlier.

This monograph is designed for the practicing chemist who seeks a convenient, single source for synthetic methods leading to carboxylic acids and their derivatives. We have attempted to include sufficient detail and examples of typical preparation to allow the reader to make a rational choice from among several alternative methods. We realize that there are certain to be synthetic procedures that we have failed to include, or have given only cursory attention. For this, we apologize, with the sincere hope that what has heen included will be of help and interest to our colleagues in the international organic chemistry community.

We wish to express our gratitude to the Department of Chemistry at Virginia Polytechnic Institute, which has been our professional home for a combined time of nearly half-a-century. To the National Science Foundation, the National Institutes of Health, and the Defense Advanced Research Project Administration, we extend our sincere appreciation for financial support of our research efforts while this monograph was being written. Finally, we thank Marion Bradley Via, without whose generosity this project would have been impossible.

Blacksburg, Virginia 1991

ix

MICHAEL A. OGLIARUSO J A M I S F. WOLFF.

Contents

1. The synthesis of carboxylic acids and esters and their derivatives 1 M. A. Ogliaruso and J. F. Wolfe

M. A. Ogliaruso and J. F. Wolfe 2. Appendix to 'The sy_nthesis of carboxylic acids and esters and their derivatives'

225

Author index 629

Subject index 671

xi