Thionyl Chloride → HCID 14461273, compound

HRID 1457309Notes

Reaction equation

HRID 1457309 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].S(Cl)([Cl:15])=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:15])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20633784-Chloro-3-methoxybenzoic acid

Product 1

HCID 14461273HCID 14461273, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-chloro-3-methoxybenzoic acid, 3.7 g, was wet down with chloroform, 3 mL, and thionyl chloride, 6 mL, was added under an argon atmosphere. The resulting paste was subjected to reflux. After several minutes, the light yellow solution was cooled to room temperature and another 4.0 g of the substituted benzoic acid was added. The mixture was again brought to reflux for one hour. A still head was added to the flask in order to distill off chloroform and excess thionyl chloride at the minimum temperature possible. The still pot residue, containing the product, then solidified. Petroleum ether, 5 mL, was added to dissolve the solid with slight heating. Upon cooling to room temperature, the mother liquor was pipetted off gently, and the remaining solid was pumped in vacuo to obtain 7.3 grams of 4-chloro-3-methoxybenzoyl chloride as a light tan solid. Another 1.03 grams of less pure material could be obtained from the mother liquor.

Workup

  1. additionwas added under an argon atmosphere
  2. temperatureto reflux
  3. waitAfter several minutes
  4. temperatureto reflux for one hour
  5. additionA still head was added to the flask in order
  6. distillationto distill off chloroform and excess thionyl chloride at the minimum temperature possible
  7. additionThe still pot residue, containing the product
  8. additionPetroleum ether, 5 mL, was added
  9. dissolutionto dissolve the solid with slight heating
  10. temperatureUpon cooling to room temperature

Sources & evidence

ORD record
ord-96b5ccf14e9e43e4af8e83dd3cb38778
Source dataset
uspto-grants-1998_12
Patent number
US05847161

Reaction notes

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