Acetic Acid → 4-Cyanobenzyl acetate

HRID 635537Notes

Reaction equation

HRID 635537 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1)#N.O.C(Cl)Cl.N([O-])=O.[Na+].[C:19]([OH:22])(=[O:21])[CH3:20]>>[C:19]([O:22][CH2:1][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 6344DichloromethaneHCID 826084-(Aminomethyl)benzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 114466294-Cyanobenzyl acetateYield 84%

Procedure

p-Cyanobenzylamine (13.2 g), water (18 g), and methylene chloride (18 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 methylene chloride, 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 14.7 g of p-cyanobenzyl acetate (yield 84%). The purity of the product was 98%.

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 methylene chloride
  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-e8120d1702624887becbb79e6cdab7f8
Source dataset
uspto-grants-2001_02
Patent number
US06187945B1

Reaction notes

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