The Hive => Chemistry Discourse => Topic started by: Niels_Bohr on March 20, 2002, 09:21:00 PM
Title: piperonal + 1-nitropropane condensation
Post by: Niels_Bohr on March 20, 2002, 09:21:00 PM
Does anyone have an idea why the yield would be poor when reacting piperonal and 1-nitropropane (as reported by Shulgin under PIHKAL #94), and if anything can be done to get this condensation to work?
Title: 3,4-MD-Phenyl-2-nitrobutene
Post by: Rhodium on March 20, 2002, 10:14:00 PM
Post 103792 (https://www.thevespiary.org/talk/index.php?topic=7493.msg10379200#msg10379200)
Title: piperonal + 1-nitropropane condensation
Post by: Nemo_Tenetur on March 21, 2002, 06:46:00 AM
Several years ago i saw in the chemical abstracts an article from a russian researcher group. they claimed that a high-pressure condensation of piperonal and 1-nitropropane greatly increased the yield.
Title: article?
Post by: Aurelius on March 21, 2002, 11:51:00 AM
can you find that article?
Title: HENRY CONDENSATION AT HIGH PRESSURES
Post by: lugh on March 21, 2002, 04:00:00 PM
Azafonov, N. E.; Sedishev, I. P.; Zhulin, V. M. Bull.Acad.Sci.USSR Div.Chem.Sci.(Engl.Transl.) 1990, 39: 4.1 738-741 Izv.Akad.Nauk SSSR Ser.Khim. 1990, : 4 829-832 The hitherto inaccessible nitroolefin (VII), which is the most convenient intermediate for the synthesis of the psychotropic amine (VIII), has been obtained by the direct condensation at high pressures (up to 1500 MPa) of piperonal (V) with 1-nitropropane (VI).The structure of (VII) was confirmed by direct synthesis from pyrocatechol (X).The amine (VIII) was obtained in three steps from (VII).This synthesis of (VIII) is shorter than that previously reported.
Title: Greatness
Post by: Aurelius on March 21, 2002, 09:00:00 PM
Lugh, you amaze aurelius sometimes. You are truly great.