Methanol → Methyl 2,3-dimethylbenzoate

HRID 1494843Notes

Reaction equation

HRID 1494843 reaction equation
[CH3:1]O.S(Cl)(Cl)=O.[CH3:7][C:8]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]>CN(C=O)C>[CH3:7][C:8]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([O:12][CH3:1])=[O:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 117822,3-Dimethylbenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 27000Methyl 2,3-dimethylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 160 ml of methanol cooled to -10° C. was dropwise added 46.4 ml of thionyl chloride while stirring. To the solution was added a mixture of 24 g of 2,3-dimethyl benzoic acid and 1 ml of DMF, and the mixture was stirred at room temperature for 4 days. After concentration, the residue was dissolved in ether. The solution was washed with water, 5% sodium carbonate, and water in this order. The solvent was evaporated and the residue was purified by vacuum distillation to obtain 25.1 g of methyl 2,3-dimethylbenzoate.

Workup

  1. additionTo the solution was added
  2. stirringthe mixture was stirred at room temperature for 4 days
  3. concentrationAfter concentration
  4. dissolutionthe residue was dissolved in ether
  5. washThe solution was washed with water, 5% sodium carbonate, and water in this order
  6. customThe solvent was evaporated
  7. distillationthe residue was purified by vacuum distillation

Sources & evidence

ORD record
ord-ca7536782c5b4e3e8f87eba570929026
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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