Methylparaben → HCID 12361498, compound

HRID 404376Notes

Reaction equation

HRID 404376 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.Br[CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CS(C)=O>[CH3:16][C:15]([CH3:17])=[CH:14][CH2:13][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 12361498HCID 12361498, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-hydroxybenzoic acid, methyl ester (17.0 mL, 66 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA), 1-bromo-3-methylbut-2-ene (12.0 g, 79 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) and potassium carbonate (23.0 g, 164 mmol) in DMSO (25 mL) was stirred at room temperature for 24 hours. EtOAc (150 mL) was added, and the mixture was washed with water (25×3 mL) and brine (25×2 mL) and dried over MgSO4. The solvent was removed, and the product was purified by CombiFlash® silica gel column chromatography, eluent with hexane/EtOAc, 90/10 to give T45.1 (12.0 g, yield 83%). 1H NMR (500 MHz, CDCl3) δ ppm 7.99 (2H, d, J=8.8 Hz), 6.92 (2H, d, J=8.8 Hz), 5.42-5.58 (1H, m), 4.57 (2H, d, J=6.8 Hz), 3.89 (3H, s), 1.81 (3H, s), 1.76 (3H, s).

Workup

  1. washthe mixture was washed with water (25×3 mL) and brine (25×2 mL)
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed
  4. customthe product was purified by CombiFlash® silica gel column chromatography, eluent with hexane/EtOAc, 90/10
  5. customto give T45.1 (12.0 g, yield 83%)

Sources & evidence

ORD record
ord-26fbb547f4844636bddafb7bcff46a5a
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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