Water → HCID 14519885, compound

HRID 1198627Notes

Reaction equation

HRID 1198627 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C-:18]#[N:19].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:18]#[N:19])=[C:4]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 14519884HCID 14519884, compound

Product 1

HCID 14519885HCID 14519885, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A two-phase mixture of crude 1-bromomethyl-4-methyl-2-phenylmethoxybenzene (21.84 g, 75 mmol), NaCN (11.0 g, 0.22 mol), tetrabutylammonium bromide (2.4 g, 7.5 mmol), water (25 ml) and CH2Cl2 (50 ml) was stirred at room temperature for 1 hour and the layers were separated. The organic layer was washed well with water to remove tetrabutylammonium salts and after drying (CaCl2) the solvent was removed to give (4-methyl-2-phenylmethoxyphenyl)acetonitrile (17.8 g, 100% crude yield) as an oil.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed well with water
  3. customto remove tetrabutylammonium salts
  4. dry with materialafter drying (CaCl2) the solvent
  5. customwas removed

Sources & evidence

ORD record
ord-a8f80ffeb88545259f4235e4286fab57
Source dataset
uspto-grants-1994_01
Patent number
US05281620

Reaction notes

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