Question

@abb0t
Can somebody help me to make a qualified guess what I might have made from the following synthesis.

Answer 1

I was trying to make phenacetin (N-(4-Ethoxyphenyl)acetamide) from p-hydrixyacetanilid, but I know something most have went wrong, I did the following thing:
I toke some sodium (s) and dissolved it in 99% ethanol, it was going to be 100% disolved, however there were still trace of sodium in solid state when p-hydrixyacetanilid was added to the mixture, the result was a dark green mixture. After letting that react ethyl iodide was added to the mixture, doing a minor color change towards a dark red / purple.

Now my question is: What chemical have might just been made in this solution.

I was thinking about that the trace of sodium (s) reacted with hydroxid group on p-hydrixyacetanilid and do a formation of alkoxides from hydroxid group, but I'm very unsure.

Answer 2

Can you draw your steps? I don't know what hydrixyacetanilid looks like :P

Answer 3

Sorry also me that wrote wrong meant p-hydroxyacetanilide, but I can try draw the conditions
See attachment.