Methylparaben → Methyl 4-(3-chloropropoxy)benzoate

HRID 1709844Notes

Reaction equation

HRID 1709844 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][Cl:16].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][Cl:16])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 12389265Methyl 4-(3-chloropropoxy)benzoateYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 30.4 g (0.2 mole) of methyl-4-hydroxybenzoate*, 63 g (0.4 mole) of 1-bromo-3-chloropropane and 82.9 g (0.6 mole) of anhydrous potassium carbonate in 1 liter of acetone was heated at reflux for 20 hr. The mixture was cooled, filtered and the filtrate concentrated to give an oil as residue. The oil crystallized when triturated with cold petroleum ether (30°-60° C.). The solid was collected by filtration and recrystallized from petroleum ether (60°-110° C.) to yield 42.9 g (94%) of title compound as a white solid, mp 56.5°-59° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customto give an oil as residue
  7. customThe oil crystallized when
  8. customtriturated with cold petroleum ether (30°-60° C.)
  9. filtrationThe solid was collected by filtration
  10. customrecrystallized from petroleum ether (60°-110° C.)

Sources & evidence

ORD record
ord-48acb05c73da4c98b6823c983d0f4dfd
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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