ChemicalBook CAS DataBase List P-N-NONYLANILINE

P-N-NONYLANILINE synthesis

9synthesis methods

Product Name:P-N-NONYLANILINE
CAS Number:37529-29-6
Molecular formula:C15H25N
Molecular Weight:219.37

124-11-8 Synthesis

124-11-8
124 suppliers
$45.00/250mg

62-53-3 Synthesis

62-53-3
681 suppliers
$10.00/1g

37529-29-6
33 suppliers
$36.20/1g

Yield:-

Reaction Conditions:

with aluminum (III) chloride;methyl tributylammonium chloride at 137 - 160; for 28.2 h;

Steps:

2

Example 2 Alkylation of Aniline Using Nonenes, Aluminum Chloride and Methyltributylammonium Chloride An apparatus similar to that described in Example 1 was charged with, in succession, aniline, nonenes and aluminum chloride under nitrogen. Stirring at 200-300 rpm was started and then solid methyltributylammonium chloride was added. Then heating to 160° C. was started. Reflux started at a pot temperature of 137.5° C. and increased steadily as the aniline was alkylated. Heating between 137-160° C. continued for 28.2 hr before the reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with 300 mL n-heptane and 200 mL methylene chloride and two phases separated. No reaction resulted when the heptane phase was washed with 500 mL water. The cautious addition of 500 mL water to the methylene chloride lower phase resulted in a strong reaction, indicating this phase contained the catalyst. The heptane phase was added to the methylene chloride phase after the reaction, and then the layers shaken and re-separated. The heptane phase was washed with an additional 500 mL water, and then 500 mL aq. ammonia (400 mL water plus 100 mL conc. aq. ammonia) prior to being dried over anhydrous sodium sulfate. The drying agent was removed by suction filtration and the filtrate condensed in vacuo (rotary evaporator, 95° C. bath, 3 mm final vacuum) to afford 70.09 g of reddish-orange oil. This was shown by GC to be mainly monononylaniline, yield 31.9%. IR analysis indicated the position of alkylation was para to the nitrogen atom.

References:

US2007/135656,2007,A1 Location in patent:Page/Page column 2-3