Methanol → Methyl 3-(4-acetyl-2-methylphenyl)acrylate

HRID 1951603Notes

Reaction equation

HRID 1951603 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])=[C:6]([CH3:15])[CH:5]=1)(=[O:3])[CH3:2].S(=O)(=O)(O)O.O.[CH3:22]O>>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]([O:14][CH3:22])=[O:13])=[C:6]([CH3:15])[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 690004523-(4-Acetyl-2-methylphenyl)acrylic acid

Product 1

HCID 66883900Methyl 3-(4-acetyl-2-methylphenyl)acrylate

Procedure

The obtained 3-(4-acetyl-2-methylphenyl)acrylic acid (657 mg, 3.22 mmol) was dissolved in methanol (20 mL). Concentrated sulfuric acid (250 μL) was added to the solution. The mixture was refluxed for 2 hours, and cooled to room temperature. Water (50 mL) was added to the solution. Methanol was removed under reduced pressure. The solution was extracted with ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and saturated brine. The organic layer was dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography with hexane/ethyl acetate (9:1, v/v) to give the desired compound (665 mg) as yellow crystalline product (yield 95%).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customMethanol was removed under reduced pressure
  3. extractionThe solution was extracted with ethyl acetate
  4. washwashed with saturated aqueous sodium bicarbonate solution and saturated brine
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography with hexane/ethyl acetate (9:1

Sources & evidence

ORD record
ord-d24e7d53c3a84fcdac73aeaf6f8c3599
Source dataset
uspto-grants-2013_03
Patent number
US08404726B2

Reaction notes

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