Sulfuric Acid → Dimethyl 4-methylphthalate

HRID 501807Notes

Reaction equation

HRID 501807 reaction equation
[CH3:1][C:2]1[CH:12]=C[C:5]2[C:6](=[O:10])[O:7][C:8](=O)[C:4]=2[CH:3]=1.S(=O)(=O)(O)O.[C:18]([O:21][CH2:22]C)(=[O:20])[CH3:19]>CO>[CH3:12][C:2]1[CH:1]=[C:19]([C:18]([O:21][CH3:22])=[O:20])[C:5](=[CH:4][CH:3]=1)[C:6]([O:7][CH3:8])=[O:10]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 880694-Methylphthalic anhydride

Product 1

HCID 88370Dimethyl 4-methylphthalate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.00 g of 5-methyl-2-benzofuran-1,3-dione was suspended in 30 mL of methanol, to which 0.2 mL of sulfuric acid was added at room temperature, and this suspension was stirred for 2.5 hours while heating it under reflux. The reaction mixture was cooled to room temperature, and poured into ice water followed by addition of ethyl acetate, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and then the solvent was distilled out under reduced pressure to yield 2.95 g of dimethyl 4-methylphthalate as light yellow oil.

Workup

  1. additionwas added at room temperature
  2. temperaturewhile heating it
  3. temperatureunder reflux
  4. customthe organic phase was separated
  5. washAfter the resultant organic phase was washed with water
  6. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-52a565fbe8c248368036be0242797284
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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