08-10-02 02:10
No 343683
3-Phenylpropionic acid (Hydrocinnamic acid) can be made in many ways (or bought for about $100/kg), and by subjecting it to Hell-Vollhardt-Zelinski reaction conditions (PBr3/Br2) you'll afford 2-Bromo-3-Phenylpropionic acid, which in turn can be reduced to 2-bromo-3-Phenyl-1-propanol (allylbenzene bromohydrin) using for example NaBH4 together with I2 or H2SO4.
By refluxing this bromohydrin lightly in dilute NaOH it will cyclize through an intramolecular Williamson etherification to form 2-benzyloxirane (allylbenzene epoxide), which finally is refluxed with LiI in EtOAc for a few hours to effect the isomerization of the epoxide to its methyl ketone; Phenyl-2-Propanone.
(Hive Bee)
08-10-02 08:31
No 343945
Any thoughts on the yield of P2P when using hydrocinnamic acid?
Doped(TM) since 19.... euhm... a long time
(Hive Bee)
08-15-02 02:40
No 345489
R-CO2H's dislike being reduced, although I've never tried DIBAL.
All in all, I would predict a somewhat low yield overall.
Even with good yields in each step, there would still be a few too many steps there (5) to be of much utility.
. . .
Rapture Tastes So Sweet.