O-Xylene → HCID 21427949, compound

HRID 1789083Notes

Reaction equation

HRID 1789083 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH2:5]([C:14](=NO)[CH:15]=C)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]CCC.[CH3:19]C1C=CC=CC=1C>C(C(CCCC)C([O-])=O)C.[Cu+2].C(C(CCCC)C([O-])=O)C>[CH2:3]([C:2](=[CH2:19])[C:1]#[N:4])[CH2:15][CH2:14][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 7855AcrylonitrileHCID 86741177HCID 86741177, compound

Product 1

HCID 21427949HCID 21427949, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 94139Hexanoic acid, 2-ethyl-, copper(2+) salt (2:1)Catalyst

Conditions

Temperature
115 °C

Procedure

A solution of 80.7 g of acrylonitrile and 5.3 g of copper(II) 2-ethylhexanoate in 250 g or o-xylene was heated to the boil (97° C.), after which 151.5 g of 99% pure alpha-nonylacrolein oxime were added dropwise in the course of 15 minutes, the temperature increasing to 115° C. during the addition. When the addition was complete, refluxing was continued for a further 10 minutes, after which the reaction mixture was cooled to -8° C. and the precipitated acrylamide was filtered off under suction. Fractional distillation of the mother liquor gave 121 g (89%) of alpha-nonylacrylonitrile of boiling point 122°-124° C./ 12 mbar.

Workup

  1. additionWhen the addition
  2. temperaturerefluxing
  3. temperatureafter which the reaction mixture was cooled to -8° C.
  4. filtrationthe precipitated acrylamide was filtered off under suction
  5. distillationFractional distillation of the mother liquor

Sources & evidence

ORD record
ord-5cc48f0a138a4dc4bcee162880e6a771
Source dataset
uspto-grants-1987_08
Patent number
US04686302

Reaction notes

Loading…