Mesitylene → 2,4,6-Trimethylphenylacetonitrile

HRID 1940262Notes

Reaction equation

HRID 1940262 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C1(S(O[CH2:15][C:16]#[N:17])(=O)=O)C=CC=CC=1.[C:18]1([CH3:26])[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=1>>[CH3:26][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[C:19]=1[CH2:15][C:16]#[N:17]

Participants

4

Reactant 3

HCID 7947MesityleneHCID 82705Acetonitrile, [(phenylsulfonyl)oxy]-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 5206982,4,6-TrimethylphenylacetonitrileYield 72.3%

Procedure

8.0 g (0.06 mol) of aluminum chloride are first introduced into 40 ml of mesitylene at 0° C. 4.1 g (0.02 mol) of phenylsulfonyloxyacetonitrile are then added, and the reaction mixture is stirred at room temperature overnight. The crude product obtained after hydrolysis is chromatographed on silica gel using dichloromethane. 2.3 g (72.3% of theory) of 2,4,6-trimethylbenzyl cyanide are isolated.

Workup

  1. customThe crude product obtained
  2. customafter hydrolysis
  3. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-58a50835298246788cd73efc178141a8
Source dataset
uspto-grants-1997_12
Patent number
US05698735

Reaction notes

Loading…