Methanol → Methyl 3-Chloro-4-methylbenzoate

HRID 448177Notes

Reaction equation

HRID 448177 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:16]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH3:16])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 788403-Chloro-4-methylbenzoic Acid

Product 1

HCID 2801405Methyl 3-Chloro-4-methylbenzoateYield 96%

Procedure

To a solution of 3-chloro-4-methylbenzoic acid (20 g, 117 mmol) in MeOH (200 mL) was added dropwise thionyl chloride (25.6 mL, 352 mmol) at 0° C. with stirring. The mixture was stirred at room temperature for 5 days. The reaction was concentrated. The residue was dissolved in EA (500 mL), washed with 10% Na2CO3 (250 mL×2), water (250 mL) and brine (250 mL), dried over Na2SO4, filtered and concentrated to afford product as a yellow solid (20.8 g, 96%).

Workup

  1. stirringThe mixture was stirred at room temperature for 5 days
  2. concentrationThe reaction was concentrated
  3. dissolutionThe residue was dissolved in EA (500 mL)
  4. washwashed with 10% Na2CO3 (250 mL×2), water (250 mL) and brine (250 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2a29fad5e0e246e2a89a50f3691d5dd2
Source dataset
uspto-grants-2013_07
Patent number
US08481590B2

Reaction notes

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