Campus Access Only
All rights reserved. This publication is intended for use solely by faculty, students, and staff of University of the Pacific. No part of this publication may be reproduced, distributed, or transmitted in any form or by any means, now known or later developed, including but not limited to photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the author or the publisher.
Date of Award
Master of Arts (M.A.)
Emerson G. Cobb
The synthesis of a keto-aldehyde from salicylaldehyde and benzaldehyde was attempted. The first step was to protect the carbonyl with a non-reactive group.
The bisulfite addition product and the 2,4-dinitrophenylhydrazone of salicylaldehyde were prepared. The methyl acetal, the sodium bisulfite addition product, and the 2,4-dinitrophenylhydrazone of benzaldehyde were also prepared.
The bisulfite addition of both aldehydes was found to be too unstable in the presence of aldehyde was recovered in each case. The methyl acetyl chloride also decomposed. This necessitated finding a more stable group to protect the aldehyde.
The 2,4-dinitrophenylhydrazone was unaffected by treatment with anhydrous aluminum chloride in both acetyl chloride and acetic anhydride. Other reactions have shown that a nitro group deactivates the benzene ring. This may be an explanation of the failure to get a Fries rearrangement or Friedel-Crafts addition.
This synthesis was not accomplished by this method, but considerable information was gained for use in further work.
Gakle, Paul Spencer. (1951). Intermediate compounds in the synthesis of lignin. University of the Pacific, Thesis. https://scholarlycommons.pacific.edu/uop_etds/1170
No Known Copyright. URI: http://rightsstatements.org/vocab/NKC/1.0/
The organization that has made the Item available reasonably believes that the Item is not restricted by copyright or related rights, but a conclusive determination could not be made. Please refer to the organization that has made the Item available for more information. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use.