Thionyl Chloride → 2,4-Dichloro-3-methoxycarbonylbenzoylchloride

HRID 2395557Notes

Reaction equation

HRID 2395557 reaction equation
[Cl:1][C:2]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([Cl:15])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:18])=O>>[Cl:1][C:2]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([Cl:15])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:18])=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 151328742,4-Dichloro-3-(methoxycarbonyl)benzoic acid

Product 1

HCID 189891562,4-Dichloro-3-methoxycarbonylbenzoylchloride

Procedure

2,4-Dichloro-3-methoxycarbonylbenzoic acid (32.37 g) and thionyl chloride (100 ml) was heated under reflux with stirring for 3 hours. The mixture was cooled and evaporated in vacuo, then re-evaporated after addition of toluene to give 2,4-dichloro-3-methoxycarbonylbenzoyl chloride (34.76 g) as a dark brown oil. This was used in the next stage without purification.

Workup

  1. temperatureunder reflux
  2. temperatureThe mixture was cooled
  3. customevaporated in vacuo
  4. customre-evaporated
  5. additionafter addition of toluene

Sources & evidence

ORD record
ord-e80269615aba4a99b68b98501f9df53a
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

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