Thionyl Chloride → 2-(3-Chloromethylphenoxy)methylquinoline

HRID 2074014Notes

Reaction equation

HRID 2074014 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]O.S(Cl)([Cl:23])=O>C(Cl)(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][Cl:23]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14650410Benzenemethanol, 3-(2-quinolinylmethoxy)-

Product 1

HCID 145017062-(3-Chloromethylphenoxy)methylquinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 14.5 g of 3-(2-quinolinylmethyloxy)benzyl alcohol in 150 ml of CHCl3 is added dropwise 7.5 ml of thionyl chloride during 10 min. The reaction mixture is stirred for 4 hours at room temperature, and then washed with NaHCO3 solution. The organic solution is separated, dried, and evaporated to 3-(2-quinolinylmethyloxy)benzyl chloride which is used without further purification in the next step.

Workup

  1. washwashed with NaHCO3 solution
  2. customThe organic solution is separated
  3. customdried
  4. customevaporated to 3-(2-quinolinylmethyloxy)benzyl chloride which
  5. customis used without further purification in the next step

Sources & evidence

ORD record
ord-76bf2468f4394968acad2d772c7fe7c9
Source dataset
uspto-grants-1990_04
Patent number
US04920132

Reaction notes

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