Sodium Cyanide → 2-(3-(2,6-Dimethylbenzyloxy)-2-methylphenyl)acetonitrile

HRID 1958858Notes

Reaction equation

HRID 1958858 reaction equation
[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([CH3:18])=[C:8]([CH:15]=[CH:16][CH:17]=1)[CH2:9][C:10]1NN=N[N:11]=1.[C-]#N.[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([CH3:18])=[C:8]([CH2:9][C:10]#[N:11])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 178424789HCID 178424789, compound

Product 1

HCID 669591112-(3-(2,6-Dimethylbenzyloxy)-2-methylphenyl)acetonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 1-(bromomethyl)-3-(2,6-dimethylbenzyloxy)-2-methylbenzene (Step D, 4.28 g, 13.41 mmol) and NaCN (0.789 g, 16.10 mmol) in dry DMF (20 ml) was heated at 120° C. for 3 hours then cooled and diluted with EtOAc (50 ml). The organic layer was washed with water (30 ml), brine, dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1) to give the title compound.

Workup

  1. temperaturethen cooled
  2. washThe organic layer was washed with water (30 ml), brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-1bda22fd116c43f9a54b19c7c6366bf0
Source dataset
uspto-grants-2013_04
Patent number
US08410154B2

Reaction notes

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