Thionyl Chloride → Methyl 3-(chlorocarbonyl)benzoate

HRID 2105182Notes

Reaction equation

HRID 2105182 reaction equation
O=S(Cl)[Cl:3].[C:5]([O:16][CH3:17])(=[O:15])[C:6]1[CH:14]=[CH:13][CH:12]=[C:8]([C:9]([O-])=[O:10])[CH:7]=1>CN(C=O)C>[CH3:17][O:16][C:5](=[O:15])[C:6]1[CH:14]=[CH:13][CH:12]=[C:8]([C:9]([Cl:3])=[O:10])[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 69512791,3-Benzenedicarboxylic acid, monomethyl ester

Product 1

HCID 15563901Methyl 3-(chlorocarbonyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
80 °C

Procedure

SOCl2 (15 mL) and dry DMF (2 drops) were added to monomethyl isophthalate (5 g, 17.7 mmol), and the reaction mixture was refluxed at 80° C. for 6 hr. The SOCl2 was removed in vacuo, and a colorless oil was obtained and used directly in the next step.

Workup

  1. customThe SOCl2 was removed in vacuo
  2. customa colorless oil was obtained

Sources & evidence

ORD record
ord-f2d0974938cf4057a5d1b21a5cf35322
Source dataset
uspto-grants-2009_08
Patent number
US07579350B2

Reaction notes

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