Water → Methyl 3-(4-methylphenyl)-2-propenoate

HRID 1272268Notes

Reaction equation

HRID 1272268 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[CH3:13]I.O>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 158353-(p-Tolyl)acrylic acid

Product 1

HCID 589472Methyl 3-(4-methylphenyl)-2-propenoateYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-methylphenyl)-2-propenoic acid (10.0 g, 61.7 mmol) in THF (100 ml) were added 1,4-diazabicyclo[5.4.0]-7-undecene (11.0 mL, 73.6 mmol) and methyl iodide (4.3 mL, 69.1 mmol) under ice cooling and the mixture was stirred at room temperature for 24 hours. The resulting mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with aqueous sodium sulfite, saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from hexane to obtain 9.10 g (yield 84%) of the title compound. mp. 56–58° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with aqueous sodium sulfite, saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-a4e3ea1675d144bfa9eb74eeec9479c7
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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