Author Topic: idea on new way to X well maby not so new  (Read 1701 times)

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quantum

  • Guest
idea on new way to X well maby not so new
« on: February 25, 2004, 08:14:00 PM »
DCM + NaI -----> DIM
catechol + DIM + hydroxide -----> 2,3 methylendioxybenzene
2,3 methylenedioxybenzene + paraformaldehyde + HCl ------> 3,4 methylenedioxybenzylchloride

3,4 methylenedioxybenzylchloride + NaCN -----> 3,4 methylenedioxybenzylcyanide
3,4 methylenedioxybenzylcyanide + Aceticanhydride ---->
MDP2P

anyway do think it would work I must admit catechol is quite
expensive but then so is X


GC_MS

  • Guest
oops
« Reply #1 on: February 25, 2004, 11:13:00 PM »
2,3 methylenedioxybenzene

More properly, this compound should be named 1,3-benzodioxole or 1,2-methylenedioxybenzene.

anyway do think it would work I must admit catechol is quite expensive but then so is X

If catechol is too expensive, you can always purchase salicylaldehyde, which costs a bit less (per mole). However, you will have to perform supplementary syntheses. Another option is obtaining phenol, which is very cheap, but you would have to perform even more supplementary syntheses. You pay more for a reason.

Also, "X" is not a product. Among chemists, you call it MDMA. You can name it "X" amongst the mobs on the streets, looking for a fun drug and ignorant about the difference between a chemical structure and a mathematical differentiation equation; but otherwise, ...  :P


quantum

  • Guest
good
« Reply #2 on: February 26, 2004, 12:27:00 AM »
if thats the only problems you can come up with thats a good thing


GC_MS

  • Guest
oops 2
« Reply #3 on: February 26, 2004, 12:47:00 AM »
Hold it... I'm not saying the other steps are valid  ;) .

I'd like to offer some advise on the methylenation of catechol though. Using diiodomethane is not necessary. Rhodium's site has a page about methylenation reactions for catechol that work just great with dichloro- and dibromomethane. Considering the fact that DCM gives reasonable to high yields in the methylenation of catechol, there is no good reason to use dibromo- or diiodomethane other than spoiling money and organic reagents. The use of a good solvent (DMF or DMSO) is of high importance...

However, if you still want to peform the methylenation reaction with DIM and catechol, here are some references to synthesize it from other substances:

triiodomethane ---> diiodomethane

Hofmann. Ann 115 (1860) 267
Butlerow. Ann Chim <3> 53 (1858) 316
Auger. CR 146 (1908) 1281
Organic Synthesis Collection Vol I p 358 (you know the website)
Nad'. Izv Akad Nauk SSSR Ser Khim (1957) 1144 (Eng translation)
Gutmann. Chem Ber 52 (1919) 213
DE Jackson. Phytochemistry 23(5) (1984) 1029
Nef. Ann 308 (1899) 325

dichloromethane ---> diiodomethane

Perkin. JCS 119 (1921) 1402 (NaI in acetone)
Laskina. Zh Prikl Khim 32 (1959) 895 (Eng translation) (NaI in benzyl alcohol)
Hoeland. Ann 240 (1887) 241 (dichloromethane and iodine)

chloroform ---> diiodomethane

Lieben. Z Chem (1868) 713


Bandil

  • Guest
I suggested this route aswell some time ago,...
« Reply #4 on: February 26, 2004, 01:31:00 AM »
2,3 methylenedioxybenzene + paraformaldehyde + HCl ------> 3,4 methylenedioxybenzylchloride

I suggested this route aswell some time ago, only with bromomethylation instead, as the proposed reaction requires alot of nasty HCl gas. There where some bees which had concerns that the MD bridge could have some trouble with the harsh reaction conditions.

The rest of the steps look allright  :)

regards
Bandil


starlight

  • Guest
more info
« Reply #5 on: February 26, 2004, 05:22:00 AM »
here is some more info for you.

Post 277264 (missing)

(starlight: "Re: piperonyl chloride ---> piperonal", Chemistry Discourse)


please be aware that this cholormethylation reaction produces products/byproducts that are significant in terms of their respiratory carcinogencity.