>most of the "product" was actually tar.
This was a very dark, but very free-flowing ketone with almost no smell. It was not nearly as viscous as normal post-15% H2SO4 hydrolysis ketone. I'm very encouraged by this method and suspect very little is tar. The ketone crystallized beautifully with bisulfite, impure ketone never does that.
>Please post yield post vacuum distillation ASAP!
I'm going to get an idea of the yield by going directly to forming the oxime. If the bisulfite crystallizes, I have almost no doubt in my mind that the oxime should crystallize as well. That way I'll get a good idea on the yield and, if I'm lucky, I can skip the vacuum distillation. My pump is long since toast, and I don't want to distill it without a vacuum as I fear that I'll only recover 80% of the ketone. Out of a possible 19.3g of ketoxime from 16.2g of isosafrole, I wonder what I'll recover.
I'll have the results in a few days if it crystallizes as I expect. The oxime takes many days in the dessicator to dry.