Methylparaben → Methyl 4-(allyloxy)benzoate

HRID 404387Notes

Reaction equation

HRID 404387 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12](Br)[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CS(C)=O>[CH2:14]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[CH:13]=[CH2:12]

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 4645407Methyl 4-(allyloxy)benzoateYield 99%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The reaction mixture of 4-hydroxybenzoic acid, methyl ester (20.0 g, 131.0 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA), allyl bromide (17.0 g, 138.0 mmol) and potassium carbonate (45.0 g, 329.0 mmol) in DMSO (30.0 mL) was stirred at room temperature for 8 hours. EtOAc (150 mL) was added, and the organic layer was washed with water (30×3 mL) and then dried over MgSO4. After filtration, the solvent was removed. The product was used in the next step without further purification, (25.0 g, yield 99%). 1H NMR (400 MHz, CDCl3) δ ppm 7.91 (2H, m), 6.86 (2H, m), 5.98 (1H, dt, J=17.2, 5.3 Hz), 5.35 (1H, dd, J=17.2, 1.6 Hz), 5.24 (1H, dd, J=10.6, 1.6 Hz), 4.52 (2H, d, J=5.5 Hz), 3.81 (3H, s).

Workup

  1. washthe organic layer was washed with water (30×3 mL)
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. customthe solvent was removed
  5. customThe product was used in the next step without further purification, (25.0 g, yield 99%)

Sources & evidence

ORD record
ord-6c24978583954d0e9759705fc2385f97
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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