Thionyl Chloride → alpha-(3-Chloromethylphenoxy)acetonitrile

HRID 345928Notes

Reaction equation

HRID 345928 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[O:6][CH2:7][C:8]#[N:9].S(Cl)([Cl:15])=O>C(OCC)C.CN(C)C=O>[Cl:15][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[O:6][CH2:7][C:8]#[N:9]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 113211372-[3-(Hydroxymethyl)phenoxy]acetonitrile

Product 1

HCID 14774148alpha-(3-Chloromethylphenoxy)acetonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 3283Diethyl EtherSolvent

Procedure

α-(3-Hydroxymethylphenoxy)acetonitrile (0.055 mol) in diethylether (150 ml) is stirred with thionyl chloride (0.060 mol) and a few drops of dimethylformamide at 40° C. for 1 hr. the solution is washed with water and brine, then evaporated to give α-(3-chloromethylphenoxy)acetonitrile as a yellow oil which is used directly in the next step.

Workup

  1. washthe solution is washed with water and brine
  2. customevaporated

Sources & evidence

ORD record
ord-dafda67b112e4e0f9bbbde9814434f37
Source dataset
uspto-grants-1991_10
Patent number
US05059610

Reaction notes

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