[Cryptonic]

Hello,

This is my first post on this site, so nice to meet you all.

I took an H-NMR spectrum of trans-Methyl cinnamate the other week, and upon examining it, there were two peaks that I just can't account for.

Here is the spectrum:


This is my data so far:
3.80ppm   RCOOCH₃
6.45ppm   R=CHCOOR
7.29-7.65ppm   C₆H₅R
7.69ppm   PhCH=R

However, I can't account for the peaks about 5.25ppm and 8.35ppm.


My procedure:
1. refluxed cinnamic acid with SOCl₂ to form cinnamoyl chloride.
2. Removed excess SOCl₂ via distillation and 2 washes of hexane, which was also distilled off.
3. refluxed cinnamoyl acid in CH₂Cl₂ with pyridine and methanol.
4. Separated with NaCHO₃ in separatory funnel into anhydrous CaCl₂.
5. removed excess CH₂Cl₂ via distillation.

So, what caused the peaks about 5.25ppm and 8.35ppm?
At first, I assumed it could be pyridine, due to the 8.35 peak, but I crossed that one off the list
Any help would be fantastic,

Thank you,
Cryptonic

[Cryptonic]

Only an Aromatic and an Amide would cause a peak around 8.3, wouldn't it?

[Cryptonic]

Alright, I'm just going to account the 8.35 and 5.25 shift to pyridine. It's the only thing I can think of!
Thanks anyways guys, let's hope it doesn't cost me too much if it's wrong.

[discodermolide]

looks like pyridine and dichloromethane.