See Post 96788 (missing)
(Professor: "real question anyone please /trans-beta-methylstyrene", Chemicals & Equipment) and the yield is advertised as 93%.
H2O2 which is 7 month old should be checked (how to: Search), it is also important to know how much light has gotten to the bottle in that lifespan, a lot of light will decompose it quicker. There is a nice simple method to check the real percentage of H2O2 and its purity somewhere on the Hive.
Technical grade 85-88% Formic acid should be good enough, eventually check the real percentage also by titration with a base or compare its weight per ml to a table in literature.
You can repeat the procedure with fresh H2O2, and take samples at intervals to use TLC on, so you can see when the conversion peaks. Then you stop stirring and proceed to the next step.
Different starting materials could need shorter or longer stirring times, the data for a certain compound are only sure after someone did a series of real testruns, like you are doing now.
Stirr your propenylbenzene, DCM and sodiumbicarbonate a bit longer perhaps, or use sodiumcarbonate.
You could also try the Rhodium/Semtexium peracetic acid procedure instead of the buffered performic, less harsh, just a little longer.
Now put the word " propenylbenzene " in the FSE, you'll get 508 hits , the first 100 will already give you a days work to study, f.e.
Post 436456 (https://www.thevespiary.org/talk/index.php?topic=7698.msg43645600#msg43645600)
(Aurelius: "Primary Carbon", Chemistry Discourse),
Post 322503 (https://www.thevespiary.org/talk/index.php?topic=8874.msg32250300#msg32250300)
(hypo: "bps and mps of various propenyl and allylbenzenes", Methods Discourse), bps and mps of various propenyl and allylbenzenes
Post 431689 (https://www.thevespiary.org/talk/index.php?topic=9948.msg43168900#msg43168900)
(FriendlyFinger: "Allylbenzene to propenylbenzene", Methods Discourse) your post on isomerization of allylbenzene.
Post 434529 (https://www.thevespiary.org/talk/index.php?topic=9857.msg43452900#msg43452900)
(FriendlyFinger: "Thanks for the references, I understand it...", Methods Discourse):
this is your own post on how you made your trans-beta-methylstyrene. You stated there:
""eventually got about 40% visually of something ---Don't get me wrong I'm not unhappy with what I did. I just don't know what I'm doing here and there.""
I hope you understand that your statement in this, your last post:
""Got B-Methylstyrene from Propiophenone and It came over at the right temp. Right on the nose and I'm impressed with the yield. ""
got me a bit worried about your obtained supposed trans-beta-methylstyrene. Or there must be a post from you about the same topic slipped through my event horizon since 21 May.
Now this answer costed me quite some time to establish, but I hope you don't see it as negative critics, just thinking in the blind, I'm not looking at a lot of chems as you do, so keep trying, this whole route should be feasible in quite good yield.
And setbacks are much more occuring than a straight one time result, so keep trying and asking. LT/
This post: Post 187637 (https://www.thevespiary.org/talk/index.php?topic=6393.msg18763700#msg18763700)
(OChem: "When substituting GAA for Formic acid...", Chemistry Discourse),
and all of the posters remarks, you will get some valuable info there.
Another tiny problem perhaps: Dal Cason used the word "modification" of Fujisawa and Deguchi's standard performic oxidation which uses acetone, so what modification is meant here? One we don't know of? Anybody knows?
The 93% yield mentioned seems exagerated, normally you may be glad to get 72-75% yield, and first time runs end up usually more in the 55-65% yields. Or did he really talk only about the trans-beta-methylstyrene conversion when giving that yield of 93%??
You should also look for a post of Ritter last year, who told us to use a special distillation apparatus called Wiped Film Evaporator, which are used in organic chemistry to produce high purity products by evaporation, distillation or stripping. Thin film evaporation is required for viscous and/or heat sensitive products. In certain cases evaporation can proceed to a dry residue or to crystal formation.
http://www.albmolecular.com/features/tekreps/vol03/no23/ (http://www.albmolecular.com/features/tekreps/vol03/no23/)
In this post he gives his ultimate procedure to obtain >80% yields in the performic oxidation.
Ask him in case you can't overcome your problems alone, he's a very saffy performic artist. :)
The Fujisawa/Deguchi performic oxidation appear in the following two CA citations - compare these originals with Dal Cason's modification:
Utilization of safrole as medical raw material. VI. New syntheses of 3,4-methylenedioxybenzyl methyl ketone.
Fujisawa, Toshiro; Deguchi, Yoshio.
Yakugaku Zasshi 74, 975-7 (1954), Chem. Abs 49:56727
Abstract
cf. C.A. 47, 3300a. A soln. of 34 g. 30% H2O2 and 150 g. 80% HCO2H was treated dropwise with 32.4 g. isosafrole in 120 ml. Me2CO below 40°C, the mixt. stirred 2 hrs. and let stand overnight, and the HCO2H and Me2CO removed in vacuo to give 61 g. residue (I).
I (30 g.) in 30 ml. MeOH and 180 g. 15% H2SO4 were heated 3 hrs., the mixt. cooled and extd. with Et2O, the ext. washed with water and 5% NaOH and distd. to give 10.3 g. (58%) 3,4-CH2O2C6H3CH2COMe (II), bp2 108-112°C; oxime, mp. 85-8°C; semicarbazone, mp. 162-3°C.
Fujisawa, Toshiro; Okada, Mitsuzo; Deguchi, Yoshio.
Patent JP31008573 (http://l2.espacenet.com/dips/viewer?PN=JP31008573&CY=gb&LG=en&DB=EPD)
CA 52:66321
Abstract
To a cooled mixt. of 34 g. 30% H2O2 and 150 g. HCO2H is dropped a mixt. of 32.4 g. isosafrole and 120 mL acetone below 40°C, kept overnight, evapd. in vacuo, 60 mL MeOH and 360 g. 15% H2SO4 added, heated on H2O bath 3 hrs., cooled, extd. with ether or C6H6, and distd. in vacuo to afford 20.6 g. 3,4-methylenedioxybenzyl methyl ketone (I), bp2 108-20°C.
I (23 g.) and 65 g. HCONH2 is heated at 190°C 5 hrs., cooled, 100 mL H2O2* added, extd. with C6H6, the ext. evapd., 8 mL MeOH and 75 mL 15% HCl added, heated on a H2O bath 2 hrs., alkalified with caustic alkali, the oil extd. with C6H6, and the ext. distd. in vacuo to afford 11.7 g. 3,4-methylenedioxyphenylisopropylamine (II), b5 122-7°.
* A classical typo in the clandestine chemistry literature. It has also been reprinted in several other publications, for example M. V. Smith's "Psychedelic Chemistry". It should read "H2O" and not "H2O2"...
This article has been abstracted/summarized in Post 437230 (https://www.thevespiary.org/talk/index.php?topic=9257.msg43723000#msg43723000)
(Rhodium: "Fujisawa/Deguchi original performic oxidation", Methods Discourse)
Studies on the Utilization of Safrole as Medical Raw Material. VII.
New Syntheses of 3,4-Methylenedioxybenzyl Methyl Ketone.
Toshiro Fujisawa and Yoshio Deguchi
Yakugaku Zasshi, Vol. 74, No 9, 975-977 (1954) (https://www.thevespiary.org/rhodium/Rhodium/pdf/mdp2p.fujisawa-deguchi.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/mdp2p.fujisawa-deguchi.pdf)
Summary
Hydrogen peroxide solution was applied to isosafrole in formic acid and the oil thereby obtained, assumed to be isosafrole glycol ester, was submitted to hydrolysis and dehydration with sulfuric acid from which the objective 3,4-methylenedioxybenzyl methyl ketone was obtained in approx. 60% yield.