Methylparaben → Methyl 4-(4-chlorobutoxy)benzoate

HRID 1709849Notes

Reaction equation

HRID 1709849 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][Cl:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:13][CH2:14][CH2:15][CH2:16][Cl:17])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutane

Product 1

HCID 14575308Methyl 4-(4-chlorobutoxy)benzoateYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 30.4 g (0.2 mole) of methyl-4-hydroxybenzoate, 68.6 g (0.4 mole) of 1-bromo-4-chlorobutane and 82.9 g (0.6 mole) of anhydrous potassium carbonate in 1 liter of acetone was heated at reflux for 17 hr. The mixture was cooled, filtered, and the filtrate concentrated under reduced pressure to give an oil which crystallized. The solid was triturated with cold petroleum ether (30°-60° C.), collected by filtration, and dried to yield 44.3 g (92%) of title compound as a white solid. An analytical sample, mp 28.5°-29° C., was prepared from petroleum ether (30°-60° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 17 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customto give an oil which
  7. customcrystallized
  8. customThe solid was triturated with cold petroleum ether (30°-60° C.)
  9. filtrationcollected by filtration
  10. customdried

Sources & evidence

ORD record
ord-68c69c2b47884835a5ac936eac489027
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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