Fife and O'Shaughnessy have made a serices of di-esters by allowing the sodium salts of various fatty acids to react with ethyl monochloracetate according to the following equation:
RCO2 Na + ClCH2 CO2 C2 H5 -----------> RCO2CH2CO2 C2 H5 + NaCL
The mechanism of the reaction appears to be ionic and to involve the attack of an RCO2- ion on the carbon atom to which the chlorine atom is attached. As the RCO2- approaches this carbon atom the chlorine atom moves away and leaves as a chloride ion. This reaction appears to be similar to the Williamson synthesis of ethers:
RONa + R'X --------------> ROR' + NaX
| Identifer | oai:union.ndltd.org:UTAHS/oai:digitalcommons.usu.edu:etd-8273 |
| Date | 01 May 1953 |
| Creators | Perkins, Richard W. |
| Publisher | DigitalCommons@USU |
| Source Sets | Utah State University |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | All Graduate Theses and Dissertations |
| Rights | Copyright for this work is held by the author. Transmission or reproduction of materials protected by copyright beyond that allowed by fair use requires the written permission of the copyright owners. Works not in the public domain cannot be commercially exploited without permission of the copyright owner. Responsibility for any use rests exclusively with the user. For more information contact digitalcommons@usu.edu. |
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