Thionyl Chloride → 1-(Chloromethyl)-4-propylbenzene

HRID 493036Notes

Reaction equation

HRID 493036 reaction equation
[CH2:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]O)=[CH:6][CH:5]=1)[CH2:2][CH3:3].S(Cl)([Cl:14])=O>C(Cl)(Cl)Cl>[CH2:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][Cl:14])=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2760472(4-Propylphenyl)methanol

Product 1

HCID 122531731-(Chloromethyl)-4-propylbenzeneYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 50 ml of chloroform was dissolved 8.63 g (57.5 mmol) of 4-n-propylbenzyl alcohol synthesized in the step (ii), and 8.10 g (68.1 mmol) of thionyl chloride was added to the mixture. The mixture was subjected to reaction at a room temperature for 24 hours. After the completion of the reaction, the chloroform phase was washed successively with an aqueous solution of sodium hydrogencarbonate and water. Chloroform was removed from the chloroform phase to give 9.40 g (55.8 mmol) of 4-n-propylbenzylchloride.

Workup

  1. additionwas added to the mixture
  2. customThe mixture was subjected to reaction at a room temperature for 24 hours
  3. customAfter the completion of the reaction
  4. washthe chloroform phase was washed successively with an aqueous solution of sodium hydrogencarbonate and water
  5. customChloroform was removed from the chloroform phase

Sources & evidence

ORD record
ord-efb9c43b1460418aabf8d823c1a5a25b
Source dataset
uspto-grants-2009_05
Patent number
US07534547B2

Reaction notes

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