Water → (4-Chloro-phenyl)-prop-2-ynyloxy-acetonitrile

HRID 1092904Notes

Reaction equation

HRID 1092904 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Cl)[O:9][CH2:10][C:11]#[CH:12])=[CH:4][CH:3]=1.[C-:14]#[N:15].[Na+].O.[OH-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:9][CH2:10][C:11]#[CH:12])[C:14]#[N:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 14798Sodium HydroxideHCID 576886121-Chloro-4-(chloro-prop-2-ynyloxy-methyl)-benzene

Product 1

HCID 57688608(4-Chloro-phenyl)-prop-2-ynyloxy-acetonitrileYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Chloro-4-(chloro-prop-2-ynyloxy-methyl)-benzene (13.0 g) is added to sodium cyanide (3.1 g) in N,N-dimethylformamide (40 ml) over 2 hours at room temperature. The reaction mixture is stirred at room temperature for 3 hours and then poured into water (200 ml), which contained sodium hydroxide (4 g). The aqueous phase is extracted with tert butyl methyl ether (2×200 ml). The organic phases are washed with water (2×50 ml), combined, dried (sodium sulfate) and evaporated. (4-Chloro-phenyl)-prop-2-ynyloxy-acetonitrile (9.2 g) is obtained which is purified by flash column chromatography on silica gel using ethyl acetate/hexane as eluant.

Workup

  1. extractionThe aqueous phase is extracted with tert butyl methyl ether (2×200 ml)
  2. washThe organic phases are washed with water (2×50 ml)
  3. dry with materialdried (sodium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-22e5d959c2244258933714477adddb34
Source dataset
uspto-grants-2012_03
Patent number
US08129560B2

Reaction notes

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