[AlphaScent]

Taking Citronellal and treating with mCPBA at 0 degrees gives the epoxide.

But in the NMR there is a small shift at 175 ppm on the C13.  I could not do a proton to look for a singlet.

I assume a small amount can go through Bayer-Villager.

Is 175 ppm too high of a shift for a formate ester??  Do not have much experience with them.

http://www.chem.wisc.edu/areas/reich/handouts/nmr-c13/cdata.htm

This source it would seem so.

[Babcock_Hall]

Ethyl formate has a shift of about 161 ppm for the carbonyl carbon, which is about the same as methyl formate.  Your shift is within a few ppm of protonated methyl formate, but that seems unlikely.

[PhDoc]

Alpha,

What scale did you do the reaction on? Was 13C crude or clean? Citronellal should be cheap, yes?

FYI, Hans Reich is rarely wrong about NMR.

[AlphaScent]

Yes, very cheap.

Have a ton of it.  Only doing it on like 10 grams now for trial reactions.

I have decided it is not the formate from Bayer-Villager.  There is no C13 shift at like 60-70 for the C-O.