Methylparaben → Methyl 4-(4-bromobutoxy)benzoate

HRID 265392Notes

Reaction equation

HRID 265392 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5]Br.[OH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 80561,4-DibromobutaneHCID 11430Potassium Carbonate

Product 1

HCID 10979046Methyl 4-(4-bromobutoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1,4 dibromobutane (50 ml), methyl 4-hydroxy-benzoate (15.2 g, 0.1 mole), potassium carbonate (40 g) in 2-butanone (500 ml) was refluxed for 24 hours. The mixture was filtered, solvent removed and the residue was chromatographed on silica gel eluted with chloroform/petrol and recrystallised from pentane to give methyl 4-(4-bromobutyloxy)benzoate (19.26 g).

Workup

  1. temperaturewas refluxed for 24 hours
  2. filtrationThe mixture was filtered
  3. customsolvent removed
  4. customthe residue was chromatographed on silica gel
  5. washeluted with chloroform/petrol
  6. customrecrystallised from pentane

Sources & evidence

ORD record
ord-70044cf59d9d4b0d84034916305dc678
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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