1-Bromo-3-chloropropane → Methyl 4-(3-chloropropoxy)-3-methoxybenzoate

HRID 1460223Notes

Reaction equation

HRID 1460223 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.Br[CH2:15][CH2:16][CH2:17][Cl:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:13][O:12][C:1](=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([O:8][CH2:15][CH2:16][CH2:17][Cl:18])=[C:4]([O:5][CH3:6])[CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 19844Methyl Vanillate

Product 1

HCID 14407173Methyl 4-(3-chloropropoxy)-3-methoxybenzoateYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 100 g (0.549 mole) of methyl vanillate, 172.8 g (1.1 mole) of 1-bromo-3-chloropropane and 228 g (1.65 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 a white solid as residue. The solid was triturated with petroleum ether, collected by filtration, and dried to yield 137.8 g (97%) of the title compound as a white powder, mp 104°-105° C. (2-propanol).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customto give a white solid as residue
  7. customThe solid was triturated with petroleum ether
  8. filtrationcollected by filtration
  9. customdried

Sources & evidence

ORD record
ord-18d0a37a83f24507b5276fed82f5c07c
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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