Chrysanthemic Acid, from the chrysanthemum flower, is a natural insecticide which has been known since ancient Persia. Its structure is that of a cyclopropane containing, irregular, monoterpene. Last year, most of the groups working on the synthesis of chrysanthemic acid were attempting to use the procedure described by Schatz in the J. Chem. Ed. article cited above, but were having trouble getting one of the reactions to work. One group found the procedure of Kelly to work fairly well. In this procedure the diene shown below was transformed in two steps to Chrysanthemic acid. Since Aldrich is discontinuing production of this diene, we need to find a method for preparing it. Never mind! Aldrich is again selling this diene! This synthesis gives a mixture of cis and trans isomers, and it would be useful to explore methods to improve the trans/cis ratio, such as using the t-butyl ester rather than the ethyl ester of the diazoacetate.
| Lab Day | Name | |
|---|---|---|
| Monday | ||
| Monday | ||
| Tuesday | ||
| Tuesday | ||
| Wednesday | Kirsten Lim | lermsten@hotmail.com |
| Wednesday | April Nelson | amnelson@ups.edu |
| Thursday Aft. | ||
| Thursday Aft. | ||
| Thursday Eve. | Kyle Putnam | kyle_lynn@hotmail.com |
| Thursday Eve. | Emily Vonk | evonk@ups.edu |
| Thursday Eve. | Julie Sunada | jsunada@ups.edu |
The table below lists the chemicals that we will have available for this project. If you need something that is not on this list, consult with the mentor for your project. Also note the "Amount/group" column. This is the total amount of material available for each group to use on the project.
| Reagent | Source | Amount/group | Location | Comments |
|---|---|---|---|---|
| 2,5-dimethyl-2,5-hexanediol | Aldrich Cat. # 14,361-8 |
15 g | TA room | No need to use this, the diene is again available. |
| Ethyl diazoacetate | Fluka Cat. # 33501 |
5 mL | TA room | |
| 2,5-dimethyl-2,4-hexadiene | Aldrich #D16,100-4 | 20 mL | TA room | |
| tert-Butyl diazoacetate | Aldrich #48,075-4 | 0.5 g | TA room |