Thionyl Chloride → 1-(Chloromethyl)-4-(octyloxy)benzene

HRID 1739407Notes

Reaction equation

HRID 1739407 reaction equation
[CH2:1]([O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]O)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].S(Cl)([Cl:20])=O>C(Cl)(Cl)Cl>[CH2:1]([O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][Cl:20])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 144261p-Octyloxybenzyl alcohol

Product 1

HCID 146742861-(Chloromethyl)-4-(octyloxy)benzeneYield 81.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.5 g of 4-octyloxybenzyl alcohol were dissolved in 20 ml of chloroform, and the resultant solution was further fed dropwise with 1.48 g of thionyl chloride and then stirred for 1 hour at room temperature. The solution reacted was poured into ice-water and extracted with chloroform. The organic layer resulted was then dried with anhydrous magnesium sulfate, and the solvent used was removed by distillation under reduced pressure, thereby affording 2.2 g of 4-octyloxybenzyl chloride.

Workup

  1. customThe solution reacted
  2. extractionextracted with chloroform
  3. customThe organic layer resulted
  4. dry with materialwas then dried with anhydrous magnesium sulfate
  5. customthe solvent used was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-414dda7150774526a14e4f13e022a9f8
Source dataset
uspto-grants-1999_10
Patent number
US05965743

Reaction notes

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