Veratryl alcohol → Veratryl chloride

HRID 1757545Notes

Reaction equation

HRID 1757545 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6]O.S(Cl)([Cl:15])=O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][Cl:15]

Participants

4

Reactant 2

HCID 7118Veratryl alcoholHCID 24386Thionyl Chloride

Product 1

HCID 81740Veratryl chlorideYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a nitrogen atmosphere, 5 g (29.73 mmol.) of 3,4-dimethoxybenzyl alcohol was dissolved in 25 ml of dichloromethane. The obtained solution was placed in an ice-bath, and to this was dropwise added a solution of 2.16 ml (29.74 mmol.) of thionyl chloride in 5 ml of methylene chloride. The mixture was then stirred at room temperature for 1 hour. The mixture was placed under reduced pressure at room temperature to distill off the solvent to give 5.624 g of the desired compound as a yellow oil.

Workup

  1. customThe obtained solution was placed in an ice-bath
  2. customwas placed under reduced pressure at room temperature
  3. distillationto distill off the solvent

Sources & evidence

ORD record
ord-8a33cc1842db4a90acbec847a1d8bef1
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

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