4-Methoxybenzyl alcohol → 4-Methyloxybenzyl chloride

HRID 2103952Notes

Reaction equation

HRID 2103952 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][CH:4]=1.O=S(Cl)[Cl:13]>O1CCOCC1>[Cl:13][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 77384-Methoxybenzyl alcoholHCID 24386Thionyl Chloride

Product 1

HCID 699934-Methyloxybenzyl chlorideYield 97.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

110 mmol 4-methoxybenzyl alcohol was dissolved in 60 ml dioxane and 150 mmol SOCl2 was slowly dropped into the solution. The solution was stirred for 3 h at 60° C. and evaporated under reduced pressure. EtOAc was added and the resulted solution was washed with water. The separated organic layer was dried and evaporated to give 107 mmol 1-(chloromethyl)-4-methoxybenzene.

Workup

  1. customevaporated under reduced pressure
  2. additionEtOAc was added
  3. washthe resulted solution was washed with water
  4. customThe separated organic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-6b6c0dc7694740b0ac971aaf4b389130
Source dataset
uspto-grants-2009_08
Patent number
US07576165B2

Reaction notes

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