Thionyl Chloride → Benzoyl chloride, 3-methoxy-2-methyl-

HRID 260806Notes

Reaction equation

HRID 260806 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:12])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](O)=[O:7].S(Cl)([Cl:15])=O>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([CH3:12])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([Cl:15])=[O:7]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 70214833-Methoxy-2-MethylBenzoic Acid

Product 1

HCID 14719554Benzoyl chloride, 3-methoxy-2-methyl-Yield 86.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 3-methoxy-2-methylbenzoic acid (454 g, 2.73 moles) in 1300 mL chloroform containing 20 g dimethyl formamide at 65° C., thionyl chloride (390 g) was added dropwise over 6 hours, whereupon the solvent was removed by evaporation at a reduced pressure. The residue (512 g) was distilled at 110° C. at 1-2 mm Hg to give 3-methoxy-2-methylbenzoyl chloride (435 g).

Workup

  1. customwas removed by evaporation at a reduced pressure
  2. distillationThe residue (512 g) was distilled at 110° C. at 1-2 mm Hg

Sources & evidence

ORD record
ord-cb926d2aa9224368b623b498e409449b
Source dataset
uspto-grants-1996_06
Patent number
US05530028

Reaction notes

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