Sciencemadness Discussion Board

Synthesis of 2-Methyl-2-butyl nitrite?

TertAmyl - 14-9-2016 at 14:02

I can't find much info on tert-pentyl nitrite (2-Methyl-2-Butyl nitrite). Can anyone confirm 2-methyl-2-butanol undergoes esterification as I've outlined it below?

The reaction from figure #1, but substituting in the molecule found on figure #2..

Figure #1:
Preparation-of-isoamyl-nitrite-isopentyl-nitrite-3-methylbutyl-nitrite-amilnitrite-vaporole.png - 22kB

Figure #2:



Quote:

Procedure:
1). A chilled solution of 100mL H2O and 25g NaNO2 is prepared.

2). A chilled solution of 19mL H2SO4 and 26mL of 2-methyl-2-butanol is prepared (Combining these is very exothermic). After the addition two layers are formed, a orange lower layer (aqueous), and a clear upper layer.

3). Sol. #1 is placed into an ice bath with stirring. Sol. #2 is added drop wise below the water line of sol. #1. (toxic oxides will evolve).

4). After the complete addition the reaction is left with stirring until bubbles cease to form. Turn off stirring, two layers should form.

5). Using a sep funnel discard the lower aqueous layer, and keep the vivid teal/blue layer on top.

6). Wash with sodium bicarbonate and salt water.



[Edited on 14-9-2016 by TertAmyl]

Bert - 14-9-2016 at 17:24

How about some documentation of your source materials...


TertAmyl - 14-9-2016 at 19:09

Quote: Originally posted by Bert  
How about some documentation of your source materials...



My lab book... It seemed reasonable (to me) that 2m2b could undergo esterification. The reaction proceeded exactly as expected - just as any other common alcohol esterification. However since I can't find much info on the molecule I am curious if this forum can provide any insight.. Specifically, I've been trying to find reference to the color of tert-amyl nitrite because what the synthesis yielded is a deep royal blue color, and I feel that would be mentioned somewhere in literature...

[Edited on 15-9-2016 by TertAmyl]

TertAmyl - 14-9-2016 at 21:32

I found reference in literature to this molecule following the path referenced.

http://www.chemsrc.com/en/cas/5156-41-2_249419.html

Wilson; Yang Chin.J.Physiol., 1930 , vol. 4, p. 392 Chem. Zentralbl., 1931 , vol. 102, # I p. 589

CuReUS - 15-9-2016 at 05:07

what is the boiling point of your product ?
according to literature,it should be 92.6'C at 760mmHg