Thionyl Chloride → Methyl 4-(chloromethyl)benzoate

HRID 231203

Reaction equation

HRID 231203 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9]O)=[CH:7][CH:6]=1)=[O:4].S(Cl)([Cl:15])=O>C(Cl)Cl>[Cl:15][CH2:9][C:8]1[CH:11]=[CH:12][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 81325Methyl 4-(hydroxymethyl)benzoate

Product 1

HCID 36664Methyl 4-(chloromethyl)benzoateYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of p-methoxycarbonylbenzyl alcohol (332.0 g, 2.0 mol) in methylene chloride (600 mL) is added thionyl chloride (380 g, 3.2 mol) dropwise over 3 hours and the reaction mixture heated at gentle reflux for 6 hours, allowing excess gases to escape. The excess thionyl chloride and methylene chloride are removed and the yellow oil triturated with hexane to yield a total of 300 g (81.5% yield) of white, solid methyl α-chloro-p-toluate, the identity of which is confirmed by elemental analysis and mass spectrum analysis as follows:

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat gentle reflux for 6 hours
  3. customThe excess thionyl chloride and methylene chloride are removed
  4. customthe yellow oil triturated with hexane

Sources & evidence

ORD record
ord-e1acda5dda51424f85d303f1dbac3770
Source dataset
uspto-grants-1989_07
Patent number
US04845187

Linked notes

Loading…