Decided to give this a try using the Aliquat 336 method instead of the IPA as the Aliquat was readily available and Barium had such high yields with it.
33,54 gr. (250 mmol) phenyl-2-propanone (note 1)
25,3 gr. (375 mmol) methylamine HCl (note 2)
11 gr. (290 mmol) sodium borohydride
4,8 gr. Aliquat 336
In a 1000 ml 3 neck RBF fitted with overhead stainless steel stirrer the ketone in 100 ml toluene was added followed by the additon of the MeNH2 mixed with 30 ml water in one portion. While stirring violently 15 gr. NaOH in 40 ml water was added dropwise over a period of 19 minutes (some ammonia scent escaping from flask at this point).
A few minutes after after the addition of the NaOH a slight pinkish hue was noticed which
seemed to get slightly darker in color as the mixture was stirred for 1 hour at room temp.
After stirring, the mixture was seperated and the aqueous layer discharged. The organic layer was a tranparent purple color. Very pretty, but not expected. Worried at this point.
The purple imine was tranferred to a 1000 ml, 3 neck RBF fitted with the mechanical stirrer used in previous procedure. Added the Aliquat 336 in approx. 4 minutes (had weighed amount in test tube- very viscous). Prepared the borohydride by placing it along with 25 mg NaOH in a beaker and added 35 ml water and swiled by hand for 3 seconds. Added this in one portion to the imine/Aliquat mix and started violent stirring. At this point an exothermic reaction ensued (noticed condensation in the flask). This was confusing as Barium used slight heating to 35 degrees. Stirring was slowed (still very fast though-enough to create emusion) and a cold water bath was applied until temp came down to 40C where it stayed fairly stable until it started to drop after about 20 minutes of stirring. Also, the purple color dissappeared after the addition of the borohydride and the mix was a somewhat cloudy white color which changed to a somewhat golden yellow color as stirring progressed.
After the reaction the residual borohydride was destroyed by adding dropwise a 20% acetic acid soln. until no gas evolved. The aqueous layer was seperated and discharged. The organic layer was extracted with 3x100ml 10% HCl, which was washed with toluene and saturated with NaCl. The soln. was then basified until pH 14. Noticed at this point that there was very little oil present. Perhaps 3-5 ml. Extracted anyway with 2x50 ml toluene which was washed with water and dilute NaCl soln. About 80 ml of the solvent was stripped off before exhaustion set in and called it a night. Suspect wise bees will say to fractionally distill ketone. Please advise and I will give this one another go. -zero
Note 1- made using store bought phenylacetic acid using xtaldocs PbO method [
https://www.thevespiary.org/rhodium/Rhodium/chemistry/p2p.paa-pb.html
] Post reaction workup consisted of:
Seperating the orgaincs in sep funnel, washing the organic layer with 20% NaOH soln. until washing were alkaline to pH paper and then washing organics with water which created a serious emulsion. The emulsion was effectively broken up by adding NaCl to the sep funnel and swirling. The aqueous portion of the post reaction mix was extracted with 2x50 ml portions of diethyl ether, and treated as per organic layer procedure above. The ether extracts were then added to main product, dried over MgSO4, and the ether stripped off. The resulting ketone was vacuum distilled but not fractionationally distilled.
Note 2-made using Vogel procedure. Recrsyallized in methanol. Clear crytals that look snow white when all together in a flask.