Methylparaben → Methyl 4-(allyloxy)benzoate

HRID 1662465Notes

Reaction equation

HRID 1662465 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), 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 phase was washed with water (30×3 mL). The organic layer was dried over MgSO4. The solvent was removed. The product thus obtained was of sufficient quality for use 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 phase was washed with water (30×3 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. customThe solvent was removed
  4. customThe product thus obtained
  5. customwas of sufficient quality for use in the next step without further purification, (25.0 g, yield 99%)

Sources & evidence

ORD record
ord-38202ffb807142979de3e112a7f3330a
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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