Thionyl Chloride → 1-(Chloromethyl)-2,3-dimethoxybenzene

HRID 1460182

Reaction equation

HRID 1460182 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]O.S(Cl)([Cl:15])=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][Cl:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 797382,3-Dimethoxybenzyl alcohol

Product 1

HCID 27583941-(Chloromethyl)-2,3-dimethoxybenzeneYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 30 ml of methylene chloride was dissolved 3.36 g (20 mmol.) of 2,3-dimethoxybenzyl alcohol. Under chilling with ice, to the solution was dropwise added a solution of 1.6 ml (22 mmol.) of thionyl chloride in 5 ml of methylene chloride for 10 min. The mixture was stirred at the same temperature and then placed under reduced pressure to distill off the solvent, to give 3.71 g of 2,3-dimethoxybenzyl chloride as a brown oil, yield 99.5%.

Workup

  1. temperatureUnder chilling with ice, to the solution
  2. distillationto distill off the solvent

Sources & evidence

ORD record
ord-fb0d730526ee4ac28be8685929e0b77f
Source dataset
uspto-grants-1991_12
Patent number
US05070089

Linked notes

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