Thionyl Chloride → 4-(Tert-butyldimethylsilyloxy)benzyl chloride

HRID 1883678Notes

Reaction equation

HRID 1883678 reaction equation
[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]O)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].S(Cl)([Cl:19])=O>>[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][Cl:19])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 10014460(4-((Tert-butyldimethylsilyl)oxy)phenyl)methanol

Product 1

HCID 113688854-(Tert-butyldimethylsilyloxy)benzyl chloride

Procedure

A mixture composed of 286 mg of 4-(tert-butyldimethylsilyloxy)benzyl alcohol and 1.75 ml of thionyl chloride was heated under reflux for 1 hour. After the thionyl chloride was distilled off from the reaction mixture under reduced pressure, its azeotropic distillation with toluene was carried out three times to remove any thionyl chloride. Thus, there was obtained 4-(tert-butyldimethylsilyloxy)benzyl chloride.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. distillationAfter the thionyl chloride was distilled off from the reaction mixture under reduced pressure, its azeotropic distillation with toluene
  4. customto remove any thionyl chloride

Sources & evidence

ORD record
ord-8960b069a9994b4e80cd38548c7744c7
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

Loading…