Performic acid oxidation of isosafrole, Posted by Lone Deranger to The Hive

A solution of 65 grams of isosafrole in 100ml of acetone was added in one 
portion to a stirred solution of 60ml of 35% H2O2 in 300g of 85% formic acid in 
a 1000 ml beaker situated in an ice-bath (both solutions was pre-cooled to -20°C 
in the freezer). Some ice was added to the reaction mixture to prevent the temp 
from rising above 40°C, (three ice-cubes was needed until the temp stabilized). 
The mixture was allowed to stir for 16 hours, whereupon it was poured into 1500ml 
of cold water. The cloudy solution was extracted with 3x100ml CH2Cl2, and the 
pooled extracts was freed from solvent by distillation. The dark red residue was 
taken up in 120 ml of methanol, and added to 700ml of 15% H2SO4 (w/v), and the 
solution was slowly refluxed for three hours. The reaction mixture was cooled and
extracted with 3x75ml CH2Cl2. The extracts were washed with 250ml of water and 
250 ml of 5% NaOH solution. The organic phase was dried over MgSO4, filtered with
suction, the filter cake washed with a little CH2Cl2, and the solvent was removed 
by distillation. The black residue was distilled with aspirator vacuum, to give
~30 ml of a yellow-brown oil (bp 115-170°C), which was redistilled to give 31g 
(44%) of an intensely yellow oil (bp 140-150°C) which gave a single spot with TLC.
