Reaction #68739

Reaction equation

N,N,N′-tricyclohexyl-para-phenylenediamine

methyl acrylate

acetic acid

→

N,N,N′-tricyclohexyl-N′-methoxypropionyl-para-phenylenediamine

Solvents

Conditions

Workup

1. 1
   OtherA 100 ml 3-neck flask was fitted with an overhead stirrer
2. 2
   Extractionextracted with aqueous sodium hydroxide
3. 3
   Washwashed three times with water
4. 4
   OtherSolvent was removed by rotary evaporation
5. 5
   OtherSome polymer precipitated
6. 6
   Otherwas removed
7. 7
   OtherSolvent was removed by rotary evaporation
8. 8
   Filtrationfiltered
9. 9
   OtherSolvent was removed by rotary evaporation
10. 10
    OtherRemaining volatiles were removed by vacuum distillation (29″, 196° C.)
11. 11
    Otherto yield a viscous, dark yellow liquid

Procedure

A 100 ml 3-neck flask was fitted with an overhead stirrer, a thermocouple and a nitrogen inlet. The flask was charged with N,N,N′-tricyclohexyl-para-phenylenediamine (27.1 g), methyl acrylate (150 ml) and glacial acetic acid (10 ml). The reaction was stirred at 82° C. until complete. The reaction mass was taken up in xylenes, extracted with aqueous sodium hydroxide and washed three times with water. Solvent was removed by rotary evaporation. The reaction mass was taken up in hexanes. Some polymer precipitated and was removed. Solvent was removed by rotary evaporation. The product was taken up in xylenes and filtered. Solvent was removed by rotary evaporation. Remaining volatiles were removed by vacuum distillation (29″, 196° C.) to yield a viscous, dark yellow liquid.

Source