Thionyl Chloride → Chloromethyl chloroisopropyl benzene

HRID 1885819Notes

Reaction equation

HRID 1885819 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:13]([CH:14]([CH3:16])[CH3:15])=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8]O>C(Cl)(Cl)(Cl)Cl>[Cl:5][C:6]1[C:13]([CH:14]([CH3:16])[CH3:15])=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8][Cl:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 145345742-Chloro-3-isopropylbenzyl alcohol

Product 1

HCID 14555442Chloromethyl chloroisopropyl benzeneYield 85.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
25 °C

Procedure

At room temperature, 29.8 g of thionyl chloride is carefully dripped into 35 g of 2-chloro-3-isopropylbenzyl alcohol in 80 ml of carbon tetrachloride. The mixture is stirred for 15 hours at 25° C. and then evaporated down. Distillation (bp 0.3 :76°-78° C.) gives 33 g of 2-chloro-3-isopropylbenzyl chloride.

Workup

  1. customAt room temperature
  2. customevaporated down
  3. distillationDistillation (bp 0.3 :76°-78° C.)

Sources & evidence

ORD record
ord-fc3b6c140b8a4c1da8960675eeae99fb
Source dataset
uspto-grants-1992_09
Patent number
US05147645

Reaction notes

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