Sodium Sulfate → 4-tert-Butylbenzonitrile

HRID 53402

Reaction equation

HRID 53402 reaction equation
S([O-])([O-])(=O)=O.[Na+].[Na+].[C:8]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].S([O-])([O-])(=O)=O.O[NH3+:26].O[NH3+]>O>[C:8]([C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:26])=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 24846Hydroxylamine sulfateHCID 703244-tert-Butylbenzaldehyde

Product 1

HCID 778834-tert-Butylbenzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

With stirring (20 rpm), a turbine dryer is charged at room temperature with 1800 parts by weight of anhydrous sodium sulfate, 365 parts by weight of 4-tert-butylbenzaldehyde and 194 parts by weight of hydroxylammonium sulfate. Following evacuation to 25 mbar, the mixture is heated to 100° C. and stirred at this temperature for 2 hours. It is subsequently heated at 125° C. for 40 minutes, during which about 82 parts by weight of water are removed by distillation. The distillation of the nitrile is then initiated and controlled by successive reduction of the pressure to 10 mbar and raising of the jacket temperature to 170° C. 300 parts by weight of 4-tert-butylbenzonitrile are obtained with an outstanding purity of ~98-99% (HPLC), along with 18 parts by weight of a less pure fraction.

Workup

  1. stirringstirred at this temperature for 2 hours
  2. customare removed by distillation
  3. distillationThe distillation of the nitrile
  4. temperatureraising of the jacket temperature to 170° C

Sources & evidence

ORD record
ord-519708dec3b74f5589276c5767db7ef4
Source dataset
uspto-grants-1997_04
Patent number
US05618965

Linked notes

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