p-Toluenesulfonic acid → Isobutyrophenone 2,4,6-Trimethylphenylimine

HRID 1797230Notes

Reaction equation

HRID 1797230 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[NH2:4].[C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=O)[CH:12]([CH3:14])[CH3:13].CC1C=CC(S(O)(=O)=O)=CC=1>>[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[N:4]=[C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:12]([CH3:14])[CH3:13]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 69132,4,6-TrimethylanilineHCID 69144Isobutyrophenone

Product 1

HCID 12980055Isobutyrophenone 2,4,6-Trimethylphenylimine

Conditions

Temperature
220 °C

Procedure

2,4,6-Trimethylaniline (16.9 mL, 120 mmol, Aldrich) was mixed with isobutyrophenone (12.0 mL, 80 mmol, Acros) and p-TsOH (1.5 g, 8.0 mmol, Aldrich). The resulting mixture was heated for 10 h at 220° C. in a flask equipped with a Dean-Stark trap. Vacuum distillation afforded two fractions: 1. unreacted starting materials, 40–48° C./40 Pa; 2. product as a yellow oil, 98–108° C./13 Pa (6.2 g, 29.2%). 1H NMR (toluene-d8, 353 K) 7.28–6.78 (m, 4H); 6.62 (s, 2H); 2.96 (septet, 1H; J=6.7 Hz); 2.07 (s, 3H); 1.97 (s, 6H); 1.23 (d, 6H; J=6.7 Hz).

Workup

  1. customequipped with a Dean-Stark trap
  2. distillationVacuum distillation
  3. customafforded two fractions
  4. custommaterials, 40–48° C./40 Pa
  5. customproduct as a yellow oil, 98–108° C./13 Pa (6.2 g, 29.2%)

Sources & evidence

ORD record
ord-58f079a94bac4476b12b024de66c90bc
Source dataset
uspto-grants-2006_04
Patent number
US07034093B2

Reaction notes

Loading…