1,2-Dichloroethane → 3-(Acetoxymethyl)benzonitrile

HRID 635538

Reaction equation

HRID 635538 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7])#N.[OH2:11].Cl[CH2:13][CH2:14]Cl.N([O-])=[O:17].[Na+]>C(O)(=O)C>[C:13]([O:17][CH2:1][C:3]1[CH:10]=[CH:9][CH:8]=[C:5]([C:6]#[N:7])[CH:4]=1)(=[O:11])[CH3:14]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 457594Benzonitrile, 3-(aminomethyl)-HCID 23668193Sodium Nitrite

Product 1

HCID 100124223-(Acetoxymethyl)benzonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

m-Cyanobenzylamine (13.2 g), water (18 g), and 1,2-dichloroethane (22 g) were mixed, and the mixture was stirred with cooling with ice. Acetic acid (18 g) was added to the mixture. Subsequently, a 20 wt % aqueous solution (51.8 g) of sodium nitrite was added dropwise to the mixture over a one hour period. The mixture was stirred at the same temperature for four hours. The reaction mixture was subjected to extraction with 1,2-dichloroethane, and the organic solvent was concentrated. Water was added to the concentrated solution, and the residual organic solvent was removed through distillation, to thereby obtain 13.7 g of m-cyanobenzyl acetate (yield 78%). The purity of the product was 97%.

Workup

  1. temperaturewith cooling with ice
  2. stirringThe mixture was stirred at the same temperature for four hours
  3. extractionThe reaction mixture was subjected to extraction with 1,2-dichloroethane
  4. concentrationthe organic solvent was concentrated
  5. additionWater was added to the concentrated solution
  6. customthe residual organic solvent was removed through distillation

Sources & evidence

ORD record
ord-fe93df3edc0e4ce399cb5aa40e46f37a
Source dataset
uspto-grants-2001_02
Patent number
US06187945B1

Linked notes

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