Author Topic: Isosafrole ---> Safrole  (Read 124 times)

bjuice

  • Pupae
  • **
  • Posts: 59
Isosafrole ---> Safrole
« on: February 22, 2013, 06:22:03 AM »
I think I've accidentally run bromosafrole through an E1 reaction and ended up with a bunch of what I think is isosafrole.  I've searched and searched but can't find any information on bringing it back to safrole.  I mean isosafrole is great at all, but I don't have much use for it as I'm working with the halo derivatives..

Also, any tips on determining if this is actually isosafrole?  It smells similar to safrole but the smell is much weaker than safrole and has a bit of a chemical smell to it.  I'm showing density at about 1.12 g/cm3 which matches with literature.  Distills at about 96C at low vacuum.

Thoughts?  ???

Also....first post!  Hello Vespiary.  The forum's great and I hope to be contributing in the near future.  ;)
« Last Edit: February 22, 2013, 06:23:48 AM by bjuice »

Whale

  • I can ride my bike with no handlebars
  • Pupae
  • **
  • Posts: 61
Re: Isosafrole ---> Safrole
« Reply #1 on: February 22, 2013, 01:56:10 PM »
Maybee this will help.
https://y47ylcppnh3afqk4.onion.to/synthetikal/forum/topic/topic_934.html

EDIT
Heres some more
Aslo running a search for "isosafrole" gets a good amt of hits. (Also welcome to the vesp)
http://127.0.0.1/talk/index.php/topic,546.msg6278/topicseen.html#msg6278
« Last Edit: February 22, 2013, 02:08:53 PM by %1 »

antibody2

  • Subordinate Wasp
  • ***
  • Posts: 158
Re: Isosafrole ---> Safrole
« Reply #2 on: February 22, 2013, 04:59:17 PM »
check the boiling point without vacuum

or

see if it forms the pseudonitrosite dimer or not by reacting it with NaNO2/H2SO4 in ether  (isosafrole will form the dimer, safrole and bromosafrole will not form the dimer)

not sure if you will have much luck going from iso > safrole but you could always run the iso (if that's what it is) through a performic oxidation or use it to form the nitropropene via the pseudonitrosite route. The yields from that rxn are almost quantitative

good luck!

Electro´S

  • Pupae
  • **
  • Posts: 95
Re: Isosafrole ---> Safrole
« Reply #3 on: February 22, 2013, 10:33:55 PM »
If you choose the pseudonitrosite pathway, Don´t forget run this reaction inside the hood.  ::)

bjuice

  • Pupae
  • **
  • Posts: 59
Re: Isosafrole ---> Safrole
« Reply #4 on: February 22, 2013, 11:14:02 PM »
1%, great link there thanks.  Looks like I probably do have isosafrole.

antibody, I hate bringing my oil bath that high, but I may do it at atmospheric pressure just to be sure.  And yeah I'm thinking about the performic route.  I'm gonna have to get new supplies which is sort of a pain cause I'm trying to wrap things up and get through this as quick as possible, but it may be worth it.  I have right around 150g of isosafrole, which could be turned into something like 100g hunny.  It would be a shame to just toss it...


Whale

  • I can ride my bike with no handlebars
  • Pupae
  • **
  • Posts: 61
Re: Isosafrole ---> Safrole
« Reply #5 on: February 22, 2013, 11:43:47 PM »
You're welcome! Also if you dont like getting your oil that hot (I know, it's a pain. Imagine if you spilled it  :o ) You can always use sand bath. It takes a bit more time to heat up but less pesky to use in the long run IMHO. (Get like a pie pan or some container that's safe to heat and put sand in. Covering it ~halfway up the flask usually works. Magnetic stirring isnt impaired either

Sand-Bath link
http://en.wikipedia.org/wiki/Sand_bath

Wizard X

  • Lord of the Realms
  • Foundress Queen
  • *****
  • Posts: 1,224
Re: Isosafrole ---> Safrole
« Reply #6 on: February 22, 2013, 11:52:08 PM »
Remember that isosafrole has trans & cis isomers http://en.wikipedia.org/wiki/Isosafrole see properties. And the ratio of trans TO cis isomers with determine the melting & boiling points.

Further ref: http://www.drugfuture.com/chemdata/isosafrole.html
Albert Einstein - "Great ideas often receive violent opposition from mediocre minds."

bjuice

  • Pupae
  • **
  • Posts: 59
Re: Isosafrole ---> Safrole
« Reply #7 on: February 23, 2013, 12:27:23 AM »
Wizard, are you saying that the isomers form a azeotrope?  Ie, they won't distill separately at their respective boiling points?

phaseolus

  • Larvae
  • *
  • Posts: 40
Re: Isosafrole ---> Safrole
« Reply #8 on: February 23, 2013, 04:57:44 AM »
I've been curious if there were a direct way to turn isosafrole into safrole. It would be thermodynamically unfavorable, not that this would be make it impossible. AFAIK the only similar reaction is the olefin metathesis/ethenolysis, but that would in effect just cleave the terminal methyl, resulting in MD-styrene (and equimolar propylene). Couldn't find any info on TFSE. Maybe the only good way to do it is to just fucking sell the isosafrole for safrole!
« Last Edit: February 25, 2013, 02:51:20 AM by phaseolus »

Wizard X

  • Lord of the Realms
  • Foundress Queen
  • *****
  • Posts: 1,224
Re: Isosafrole ---> Safrole
« Reply #9 on: February 23, 2013, 05:44:17 AM »
Wizard, are you saying that the isomers form a azeotrope?  Ie, they won't distill separately at their respective boiling points?

Fractional distillation is necessary.

Fractional distillation. http://en.wikipedia.org/wiki/Fractional_distillation
Albert Einstein - "Great ideas often receive violent opposition from mediocre minds."