Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: PhCH2NO2 from PhCH2OH
whupharm_xu
Harmless
*




Posts: 20
Registered: 28-7-2004
Member Is Offline

Mood: No Mood

sad.gif posted on 11-9-2006 at 00:38
PhCH2NO2 from PhCH2OH


we take the following procedure in preparing PhCH2NO2 from PhCH2OH.
To a solution of benzyl alcohol in CH2Cl2 was added NaNO2. To this mixture was added HOAc and left at r.t. for 5 minutes.Then concd HCl was aded to this mixture and left without stirring for about 14 h. Two points was found in TLC plate with Rf 0.9 and 0.6, and the corresponding products were PhCH2ONO and PhCHO respectively.The procedure was taken entirely according to a paper in SYNLETT(2000,7,1064),but in fact the aim product was not obtained.
now we don't know what happened in our experiment, anybody can give me some suggestions?
View user's profile Visit user's homepage View All Posts By User
solo
International Hazard
*****




Posts: 3975
Registered: 9-12-2002
Location: Estados Unidos de La Republica Mexicana
Member Is Offline

Mood: ....getting old and drowning in a sea of knowledge

[*] posted on 11-9-2006 at 02:42


Reference Information

Note:deleted due to it's being flawed and untrue..............so save your chems for a better formula..........

A Simple and Highly Efficient Procedure for the Preparation of Aliphatic Nitro Compounds Directly from Alcohols
Baruah, Apurba; Kalita, Biswajit; Barua, Nabin C.
SYNLETT(2000,7,1064)


Abstract:
A series of enantioenriched 4-hydroxy-1-alkenyl carbamates
was prepared by (-)-sparteine-mediated homoaldolization.
These were transformed into unsaturated oxacycles, involving simple
synthetic transformations, with ring-closing metathesis (RCM)
as the key step.

[Edited on 11-9-2006 by solo]

[Edited on 11-9-2006 by solo]




It's better to die on your feet, than live on your knees....Emiliano Zapata.
View user's profile View All Posts By User
Vitus_Verdegast
Hazard to Others
***




Posts: 297
Registered: 5-12-2004
Location: Ottoman Empire
Member Is Offline

Mood: tea time

[*] posted on 11-9-2006 at 08:04


Quote:

To a solution of benzyl alcohol in CH2Cl2 was added NaNO2


You will only obtain benzyl nitrite using this procedure. Using DMF instead should give you a mixture of benzyl nitrite and alpha-nitrotoluene.

Kornblum, New Synthesis of Aliphatic Nitro Compounds J. Amer. Chem. Soc. 78, 1497 (1956)
http://www.erowid.org/archive/rhodium/chemistry/nitroalkane....




Sic transit gloria mundi
View user's profile View All Posts By User
Nicodem
Super Moderator
*******




Posts: 4230
Registered: 28-12-2004
Member Is Offline

Mood: No Mood

[*] posted on 11-9-2006 at 09:29


That Synlett paper was debunked as bullshit by some other authors some time later. Search in the next volumes of the journal, it is there somewhere. I can't even believe such an obvious hoax paper ever went trough the peer review system.
It is known for more than a century that alcohols, NaNO2 and HCl gives alkyl nitrites, so it is beyond my imagination what kind of idiotic peer review could given a green light to such a paper.




…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)

Read the The ScienceMadness Guidelines!
View user's profile View All Posts By User
whupharm_xu
Harmless
*




Posts: 20
Registered: 28-7-2004
Member Is Offline

Mood: No Mood

[*] posted on 11-9-2006 at 18:38


thank you for all!
Now my first thing is to find an easy and efficient method in preparing PhCH2NO2 using PhCH2OH. the procedure of the jacs paper(1956) is not promising for preparing PhCH2NO2, the low yield and high cost (using PhCH2Br and DMF) were its great disadvantages.
View user's profile Visit user's homepage View All Posts By User
tr41414
Hazard to Self
**




Posts: 56
Registered: 14-9-2006
Location: EU
Member Is Offline

Mood: No Mood

[*] posted on 16-9-2006 at 14:42


I belive that PhCH2OH + HCl > PhCH2Cl + H2O, PhCH2Cl + NaNO2 > PhCH2NO2 + PhCH2ONO (byproduct) + NaCl will work, if done as two separate reactions... The references for both reactions can be found in Rhodium archive...

http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/b...

http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/n...
Not really the case of benzylchloride, but should be similiar...
View user's profile Visit user's homepage View All Posts By User

  Go To Top