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

HRID 1739403Notes

Reaction equation

HRID 1739403 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([CH2:16]O)=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:22])=O>C(Cl)(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([CH2:16][Cl:22])=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 540346054-(4-Phenylbutoxy)benzyl alcohol

Product 1

HCID 151155321-(Chloromethyl)-4-(4-phenylbutoxy)benzeneYield 102.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.9 g of 4-(4-phenylbutyloxy)benzyl alcohol were dissolved in 30 ml of chloroform, and 1.6 g of thionyl chloride were further fed dropwise to the resultant solution. The solution was then stirred for 1 hour at room temperature. After completed the reaction, the solution reacted was poured into ice-water and extracted with chloroform. The organic layer resulted was dried with anhydrous magnesium sulfate, and the solvent used was removed by distillation under reduced pressure, thereby affording 3.2 g of 4-(4-phenylbutyloxy)benzyl chloride.

Workup

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

Sources & evidence

ORD record
ord-e90f10463560454484813b7b1dbc222d
Source dataset
uspto-grants-1999_10
Patent number
US05965743

Reaction notes

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