Some compounds derived from chloroacetone

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NORTHWESTERN UNIVERSITY

SOME COMPOUNDS DERIVED FROM CHLOROACETONE

A DISSERTATION SUBMITTED TO THE GRADUATE SCHOOL IN PARTIAL FULFILLMENT OF THE REQUIREMENTS for the degree DOCTOR OF PHILOSOPHY

DEPARTMENT OF CHEMISTRY

BY CHARLES HUSTON RECTOR, JR.

EVANSTON, ILLINOIS AUGUST, 1942

ProQuest Number: 10101871

All rights re s e r v e d INFORMATION TO ALL USERS The qu ality o f this r e p r o d u c t io n is d e p e n d e n t u p o n t h e quality o f t h e c o p y s u b m itte d . In t h e unlikely e v e n t t h a t t h e a u th o r did n o t s e n d a c o m p l e t e m a n u s c r ip t a n d t h e r e a r e missing p a g e s , t h e s e will b e n o t e d . Also, if m a te ria l h a d to b e r e m o v e d , a n o t e will i n d ic a te t h e d e le tio n .

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ACKNOWLEDGMENT

The author wishes to express his appreciation to Dr. Charles D. Hurd for his interest, valuable suggestions, and encouragement during the course of this investigation. The author also wishes to express his appreciation to E. I. du Pont de Nemours and Company for the Fellowship ’which made this work possible.

TABLE OF CONTENTS page HISTORICAL INTRODUCTION........ . .................. 1 Scope of the present investigation................... 18 DISCUSSION OF RESULTS............ . ............. 19 Preparation of chloroacetone cyanohydrin..... 19 Preparation of methyl £*-hydroxy-/?-chloroisobutyrate............................. . ............ 21 ^Hydroxy-/9-chloroisobutyric a c i d • 22 Acetylation of chloroacetone cyanohydrin and methyl o