https://www.thevespiary.org/rhodium/Rhodium/chemistry/oxone.epoxidation.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/oxone.epoxidation.html)
Chromic,
, but I do believe that Uemura and twodogs have.
Just for the bees who still don't want to believe! Yes, the anethol expoxide thermal arrangement works very well, it works also for the crude epoxide.
The temperature of the boiling epoxide/ketone was 265-270DegC. Vapour temp about 5DegC less.
Let uemura add another evidence test for anethole ketone: Put into the freezer (-20DegC), the ketone should cristallise after some time if it's pure enough.
Carpe Diem
There might be other OTC methods to hydrolyze the epoxide... more experimentation is definitely needed in this area. I don't know who has tried the LiI rearrangement, a quick search with TFSE revealed nothing but talk... https://www.thevespiary.org/rhodium/Rhodium/chemistry/guest.phenylacetone.txt (https://www.thevespiary.org/rhodium/Rhodium/chemistry/guest.phenylacetone.txt)
is a good read of a description of dimethoxypropenylbenzene epoxide being rearranged with LiI in EtOAc.
In 228754 Ritter says:
>Rhodium, (I have) never run the epoxide rearrangement with LiI.
A good read on the synthesis of LiI by Ritter is in Post 228375 (https://www.thevespiary.org/talk/index.php?topic=11411.msg22837500#msg22837500)
(Ritter: "Re: Ketones from Propenylbenzenes via the di-bromides", Novel Discourse). But, more importantly, there has got to be other salts (likely hard Lewis acid cation / soft Lewis base anion) that would affect the rearrangement in good yield.
I think i'm gonna take VL_'s back on the thermal ATM rearrangement issue as per the results of Post 264485 (https://www.thevespiary.org/talk/index.php?topic=8999.msg26448500#msg26448500)
(Vibrating_Lights: "Thermal isosafrole epoxide rearrangement trials", Methods Discourse).
backburner70!
Did you check Uemuras first write-up on the anethole ketone in Post 243262 (https://www.thevespiary.org/talk/index.php?topic=8989.msg24326200#msg24326200)
(uemura: "Epoxide Rearrangement Example", Methods Discourse)?
Rearrangement
The crude! epoxide was loaded together with some boiling stones in a 250ml flask equipped with a small Liebig condensor. The flask is heated by means of an electric mantel. At 260DegC (760Torr adjusted) the epoxide starts to boil (measured inside the liquid). Some 'spurious explosions' caused by the bumping stones or epoxide happened without getting out of control. The reflux is continued for 90min, the inside temperature stayed at 263DegC.
After cooling down a normal pressure destillation setup was performed. The flask was heated again and between 255 and 275Degc (*) 19g of a clear yellow-green oil came over. Then the temperature dropped down, a red-brown liquid remained in the destillation flask (Temp liquid > 283DegC). This is a yield of 19g ketone from 30ml olefine, approx. 57% yield which isn't really good but isn't bad either. (**).
A bisulfite test with 1ml of the received destillate worked like a super-duper-easy confirmation, no oily precipitae, after 20sec shaking pure bisulfite compound (light yellow in white gel) appeared.
There was indeed a brown-red residue, likely the glykol. But not tar, neither had problems with clean-up later.
Here is a typical pic of the apparatus used for rearrangement (this time not a Liebig, but just an air cooled condenser)
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000260568-file_fs7m.jpg)
The anethole ketone is a yellow oil which solifies in the freezer:
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000260568-file_vdym.jpg)
Carpe Diem