Preparation of Aryl Diethyl Phosphate Esters
Location
CSU Ballroom
Start Date
16-4-2013 10:00 AM
End Date
16-4-2013 12:00 PM
Student's Major
Chemistry and Geology
Student's College
Science, Engineering and Technology
Mentor's Name
Michael Lusch
Mentor's Department
Chemistry and Geology
Mentor's College
Science, Engineering and Technology
Description
When reducing simple phenols to a desired aromatic hydrocarbon in synthetic chemistry, the 2-step Kenner and Williams method was a reliable method. Step one of this method converts the phenol to an aryl diethyl phosphate ester. This step however uses the banned, ozone depleting, Carbon Tetrachloride. So an alternative chlorinating reagent must be found. N-Chlorosuccnimide (NCS) is the examined substitute, which is shown to work in previous studies in the laboratory of Dr. Michael J. Lusch. The concern for this experiment is that previous articles cited within the Kenner and Williams method attempted to reduce methyl salicylate and received only 20% yield. The phenol used for this researched experiment was phenyl salicylate, which is a similar molecule except replacing a methyl group with an aromatic ring. So my experiment attempted to convert phenyl salicylate to an aryl diethyl phosphate ester using the NCS method. After going through the reaction and going through the purification, such as rotary evaporator and flash chromatography, the sample is put in a NMR. The crude yield was95%, and using the both H-NMR and C13-NMR, it was determined that the desired 2-(carbo phenoxy) phenyl diethyl phosphate was present and fairly pure. Although the desired compound was made successfully, that was only step one of the Kenner and Williams method and these results cannot be compared until we complete step 2. Further experimenting to find an alternative to step 2 is needed to complete this method and finish the comparison, but the results look promising.
Preparation of Aryl Diethyl Phosphate Esters
CSU Ballroom
When reducing simple phenols to a desired aromatic hydrocarbon in synthetic chemistry, the 2-step Kenner and Williams method was a reliable method. Step one of this method converts the phenol to an aryl diethyl phosphate ester. This step however uses the banned, ozone depleting, Carbon Tetrachloride. So an alternative chlorinating reagent must be found. N-Chlorosuccnimide (NCS) is the examined substitute, which is shown to work in previous studies in the laboratory of Dr. Michael J. Lusch. The concern for this experiment is that previous articles cited within the Kenner and Williams method attempted to reduce methyl salicylate and received only 20% yield. The phenol used for this researched experiment was phenyl salicylate, which is a similar molecule except replacing a methyl group with an aromatic ring. So my experiment attempted to convert phenyl salicylate to an aryl diethyl phosphate ester using the NCS method. After going through the reaction and going through the purification, such as rotary evaporator and flash chromatography, the sample is put in a NMR. The crude yield was95%, and using the both H-NMR and C13-NMR, it was determined that the desired 2-(carbo phenoxy) phenyl diethyl phosphate was present and fairly pure. Although the desired compound was made successfully, that was only step one of the Kenner and Williams method and these results cannot be compared until we complete step 2. Further experimenting to find an alternative to step 2 is needed to complete this method and finish the comparison, but the results look promising.
Recommended Citation
Mebratu, Selam. "Preparation of Aryl Diethyl Phosphate Esters." Undergraduate Research Symposium, Mankato, MN, April 16, 2013.
https://cornerstone.lib.mnsu.edu/urs/2013/poster-session-A/34
