Thionyl Chloride → 4-Chloromethyl-1,2-diethoxy-benzene

HRID 1169504Notes

Reaction equation

HRID 1169504 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH2:7]O)[CH3:2].S(Cl)([Cl:17])=O>C1(C)C=CC=CC=1.N1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH2:7][Cl:17])[CH3:2]

Participants

6

Reactant 2

HCID 24386Thionyl ChlorideHCID 8540533,4-Diethoxybenzyl alcohol

Product 1

HCID 24348314-Chloromethyl-1,2-diethoxy-benzene

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3,4-diethoxybenzyl alcohol (736 mg) dissolved in toluene (10 ml) were added pyridine (one drop) and thionyl chloride (0.41 ml), and the resulting mixture was stirred at room temperature for 20 minutes. The reaction mixture was diluted with ethyl acetate and the resulting mixture was washed with water, an aqueous saturated solution of sodium hydrogen carbonate and an aqueous saturated solution of sodium chloride, and was dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain 3,4-diethoxybenzyl chloride (802 mg) as an oil.

Workup

  1. washthe resulting mixture was washed with water
  2. dry with materialan aqueous saturated solution of sodium hydrogen carbonate and an aqueous saturated solution of sodium chloride, and was dried with anhydrous magnesium sulfate
  3. customThe resulting organic layer was evaporated under reduced pressure
  4. customto remove the solvent

Sources & evidence

ORD record
ord-77130ba029794686932449271b456b3a
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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