Methylparaben → Methyl 4-(decyloxy)benzoate

HRID 417770

Reaction equation

HRID 417770 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CC#N>[CH2:19]([O:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]([O:8][CH3:7])=[O:17])=[CH:11][CH:12]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 81731-BromodecaneHCID 11430Potassium Carbonate

Product 1

HCID 3574987Methyl 4-(decyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Anhydrous K2CO3 (18.43 g, 0.13 mol) was added to 300 mL of CH3CN, and the solution was degassed with N2 for 20 minutes. Methyl-4-hydroxybenzoate (6.27 g, 41.2 mmol) was added to the reaction flask, which was heated to 70° C., following which 1-bromodecane (8.8 mL, 42.5 mmol) was added. The above solution was refluxed for 12 hours, and upon cooling the solvent was removed under reduced pressure. The residue was taken in CH2Cl2 (200 mL) and washed with 1 M HCl (100 mL). The organic layer was washed with distilled H2O (100 mL), and the solvent was removed under reduced pressure. Yield 12.0 g (quant.). 1H NMR: δH (CDCl3; 300 MHz): 0.90 (3

Workup

  1. customthe solution was degassed with N2 for 20 minutes
  2. additionwas added
  3. temperatureThe above solution was refluxed for 12 hours
  4. temperatureupon cooling the solvent
  5. customwas removed under reduced pressure
  6. washwashed with 1 M HCl (100 mL)
  7. washThe organic layer was washed with distilled H2O (100 mL)
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0dadccc784584837a43049a96126610d
Source dataset
uspto-grants-2012_01
Patent number
US08092712B2

Linked notes

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