Also, wanted to post and update on the reaction I did yesterday.
So I set 4 reactions, with varying amounts of DMP and keeping the 3-chloro-1,2-propane-diol amount the same. I added 0 (control), 2, 4, and 6 molar equivalents of DMP. I then added CH2Cl2 up to the same amount in each vial. Interestingly, immediately upon addition of DMP there was a precipitate formed in the 2 eq tube, and slight cloudiness to tubes with 4, and 6 eq. After 4 hours all tubes were clear except the tube with 2 eq. I spotted each on TLC after 4 hours (but haven't runt hem yet, not in the lab today) and let them go, will check them tomorrow and spot TLC again. I will do a general stain and a DNP staining that is for carbonyls.
I'll update tomorrow but thought it was interesting that the more DMP was added, the less precipitate was formed.