Thionyl Chloride → 3,4,5-Trisbenzyloxybenzyl Chloride

HRID 1760894Notes

Reaction equation

HRID 1760894 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:16]O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(OCC)C>[CH2:5]([O:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:16][Cl:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11407668(3,4,5-Tris(benzyloxy)phenyl)methanol

Product 1

HCID 225932383,4,5-Trisbenzyloxybenzyl Chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

40.0 g (0.33 mol) of thionyl chloride are added dropwise at room temperature to a suspension of 12.0 g (0.028 mol) of 3,4,5-trisbenzyloxybenzyl alcohol in 100 ml of diethyl ether. Heating is then carried out at reflux for 2 hours, resulting in a clear solution. After removal of excess thionyl chloride and solvent, the residue is recrystallised from isopropanol/hexane.

Workup

  1. temperatureHeating
  2. temperatureat reflux for 2 hours
  3. customresulting in a clear solution
  4. customAfter removal of excess thionyl chloride and solvent
  5. customthe residue is recrystallised from isopropanol/hexane

Sources & evidence

ORD record
ord-efbda141e8764053aec25cfda974ff12
Source dataset
uspto-grants-2005_01
Patent number
US06846492B2

Reaction notes

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