Dimethylformamide → Methyl 3,4-dimethylbenzoate

HRID 1808325Notes

Reaction equation

HRID 1808325 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([OH:11])=[O:10].[CH3:16]N(C)C=O>CO>[CH3:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([O:11][CH3:16])=[O:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 120733,4-Dimethylbenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 520902Methyl 3,4-dimethylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thionyl chloride (80 ml; 2 equiv.) was added at room temperature to a solution of 3,4-dimethylbenzoic acid (35 g; 1 equiv.) and dimethylformamide (1 ml) in 227 ml of methanol. The resulting reaction mixture was stirred for 12 h at room temperature and then concentrated under reduced pressure. The resulting residue was taken up in dichloromethane and washed with 5% sodium carbonate solution. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The methyl 3,4-dimethylbenzoate so obtained (38.2 g) was used in the next stage without further purification.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated under reduced pressure
  3. washwashed with 5% sodium carbonate solution
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b867b2b88ab94eda9ab96fcea42db9d8
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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