Methanol → Methyl 2-chloro-6-methylbenzoate

HRID 577213Notes

Reaction equation

HRID 577213 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:12]O>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

4

Reactant 2

HCID 887MethanolHCID 888702-Chloro-6-methylbenzoic acid

Product 1

HCID 22935202Methyl 2-chloro-6-methylbenzoateYield 71%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A mixture of 2-chloro-6-methylbenzoic acid (4.0 g, 23.4 mmol) in methanol (50 mL) and a few drops of concentrated sulfuric acid were stirred at reflux for 5 hours. After cooling to room temperature, methanol was evaporated, and the residue was dissolved in ethyl acetate (50 mL). The solution was extracted with saturated NaHCO3 (3×50 mL). The organic layer was dried over MgSO4, filtered, evaporated, and dried in vacuo, affording methyl 2-chloro-6-methylbenzoate (3.07 g, 71% yield). The product was used without further purification.

Workup

  1. temperatureat reflux for 5 hours
  2. custommethanol was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  4. extractionThe solution was extracted with saturated NaHCO3 (3×50 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-77874ba847814ae18ab1c5d0517edcc4
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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