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

HRID 346236Notes

Reaction equation

HRID 346236 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1.Br[CH2:15][CH2:16][CH2:17][Cl:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][C:9]([O:10][CH2:15][CH2:16][CH2:17][Cl:18])=[C:6]([O:7][CH3:8])[CH:5]=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 methylvanillate, 172.8 g (1.1 mole) of 1-bromo-3-chloropropane and 228 g (1.65 mole) of anhydrous potassium carbonate in 1 L 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 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-d86059b6d00f42b0a301555c2606198c
Source dataset
uspto-grants-1991_10
Patent number
US05061720

Reaction notes

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