1-Chloro-4-(chloromethyl)benzene → 4-Chlorobenzyl cyanide

HRID 1906313Notes

Reaction equation

HRID 1906313 reaction equation
[C-:1]#[N:2].[Na+].[Cl:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Cl)=[CH:7][CH:6]=1>[Cl-].C([N+](CCCC)(CCCC)CC1C=CC=CC=1)CCC.O>[Cl:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][C:1]#[N:2])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 8929Sodium Cyanide

Product 1

HCID 2415824-Chlorobenzyl cyanideYield 91%

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

196 g (4 mol) of sodium Cyanide, 12.5 g (40 mmol) of tributylbenzylammonium chloride and 660 mL of water are initially introduced into a 2 l multineck apparatus with reflux condenser, internal thermometer and dropping funnel, and the mixture is heated to 90° C. At the same temperature, 644 g (4 mol) of molten 4-chlorobenzyl chloride are added dropwise in 1 h, and the mixture is then stirred for 2 h. After having been cooled to about 35° C., the organic phase is separated off, washed with water and fractionated over a short column. 552 g of 4-chlorobenzyl cyanide (91% of theory) are obtained.

Workup

  1. temperaturewith reflux condenser
  2. temperatureAfter having been cooled to about 35° C.
  3. customthe organic phase is separated off
  4. washwashed with water

Sources & evidence

ORD record
ord-7ab43517071b4c58bdbbc926ff8f6e65
Source dataset
uspto-grants-1987_03
Patent number
US04650910

Reaction notes

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