Toluene → HCID 22146252, compound

HRID 1823701Notes

Reaction equation

HRID 1823701 reaction equation
[CH3:1][CH:2]([CH2:17][CH3:18])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:12][CH:13]([CH3:16])[CH2:14][CH3:15].C(#N)C.[Br:22]N1C(=O)CCC1=O.C1(C)C=CC=CC=1>O>[CH3:1][CH:2]([CH2:17][CH3:18])[CH2:3][O:4][C:5]1[CH:10]=[C:9]([Br:22])[CH:8]=[CH:7][C:6]=1[O:11][CH2:12][CH:13]([CH3:16])[CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6342Acetonitrile2×HCID 67184N-bromobutanimideHCID 22146239HCID 22146239, compound

Product 1

HCID 22146252HCID 22146252, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

1,2-Bis(2-methylbutyloxy)benzene (338 g, 1.35 mol) together with 2.5 l of acetonitrile was placed in a reaction vessel, cooled to 0° C. and admixed with 264 g (1.48 mol) of N-bromosuccinimide. The mixture was warmed to RT and stirred for another 90 minutes. After taking off the acetonitrile, the residue was admixed with toluene and water and the phases were separated. After shaking the aqueous phase with toluene and drying the organic phase over Na2SO4, the toluene was taken off. The crude product was purified by double fractional distillation under reduced pressure. This gave the product as a colorless oil (145° C., 1.3 mbar): 275 g (62%).

Workup

  1. temperatureThe mixture was warmed to RT
  2. customthe phases were separated
  3. stirringAfter shaking the aqueous phase with toluene
  4. dry with materialdrying the organic phase over Na2SO4
  5. distillationThe crude product was purified by double fractional distillation under reduced pressure

Sources & evidence

ORD record
ord-4e6c824e384947cba43c6849e5aab398
Source dataset
uspto-grants-2006_05
Patent number
US07041388B1

Reaction notes

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