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2.4. Piperonal from pepper
2.4.1. Oxidative cleavage of piperine by ozonolysis
A stream of ozone gas, generated by a HAILEA HLO-100 Ozone Steriliser
(100 mg of ozone per hour), was passed through a solution of piperine (1.00 g,
3.51 mmol) in a 5% solution of water in acetone. After 8 h, the ozone generator was
switched off and the solution extracted with two 10 mL portions of diethyl ether.
The combined ether extracts were dried over anhydrous sodium sulphate and the
solvent evaporated in vacuo yielding bright yellow oil. Yield: 508 mg (97%).
1
H
NMR: see Fig. S13. GC–MS: see Fig. 2.
2.4.2. Oxidative cleavage of piperine with aqueous KMnO4in THF
An aqueous solution of KMnO4(2.00 g, 12.6 mmol in 40 mL of water) was added
dropwise over a period of 4 h to a solution of piperine (1.00 g, 3.51 mmol in 40 mL of
THF) at 60 8C. After the solution had been added, the mixture was stirred for 4 h
before the MnO2precipitate that had formed was filtered off leaving a pale yellow
solution. The sample was extracted with diethyl ether and the combined extracts
were dried over anhydrous sodium sulphate. The ether was evaporated in vacuo to
yield a dark yellow-orange oil that solidified on cooling. Yield: 340 mg (65%).
1
H
NMR: see Fig. S14. GC–MS: see Fig. 2
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ref:
Synthesis and impurity profiling of MDMA prepared from commonly available
starting materials
Ryan Gallagher, Ronald Shimmon, Andrew M. McDonagh*
Centre for Forensic Science, University of Technology Sydney, Sydney, NSW 2007, Australia |