Water → 3-Methanesulfonyl-2-(2,4,6-trimethylphenyl)acrylonitrile

HRID 992669Notes

Reaction equation

HRID 992669 reaction equation
O[CH:2]=[C:3]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[CH3:14])[C:4]#[N:5].[CH3:15][S:16](Cl)(=[O:18])=[O:17].O>N1C=CC=CC=1>[CH3:15][S:16]([CH:2]=[C:3]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[CH3:14])[C:4]#[N:5])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 701428183-Hydroxy-2-(2,4,6-trimethylphenyl)acrylonitrile

Product 1

HCID 536820093-Methanesulfonyl-2-(2,4,6-trimethylphenyl)acrylonitrileYield 105.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of intermediate 1 (1 g) in 10 ml pyridine was cooled to 0° C. under nitrogen and then treated with methanesulfonyl chloride (0.67 g) with good stirring. The solution was allowed to come to room temperature and stirred for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with 1 M HCl, water and brine, dried (MgSO4) and concentrated to give 3-methanesulfonyl-2-(2,4,6-trimethylphenyl)acrylonitrile (intermediate 2) as a brown solid (1.4 g).

Workup

  1. customto come to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with 1 M HCl, water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4a1ab7b22da04e8cb2b7f43876ad3038
Source dataset
uspto-grants-2002_10
Patent number
US06469166B2

Reaction notes

Loading…