1-Bromo-3-chloropropane → 4-(3-Chloropropoxy)-3-methoxybenzeneacetic acid ethyl ester

HRID 1460225Notes

Reaction equation

HRID 1460225 reaction equation
[C:1]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.Br[CH2:17][CH2:18][CH2:19][Cl:20].C(=O)([O-])[O-].[K+].[K+]>>[CH2:14]([O:13][C:1](=[O:12])[CH2:2][C:3]1[CH:11]=[CH:10][C:8]([O:9][CH2:17][CH2:18][CH2:19][Cl:20])=[C:5]([O:6][CH3:7])[CH:4]=1)[CH3:15]

Participants

4

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 108965Ethyl homovanillate

Product 1

HCID 144071784-(3-Chloropropoxy)-3-methoxybenzeneacetic acid ethyl esterYield 65.1%

Procedure

A mixture of 50 g (0.238 mole) of ethyl homovanillate (98%), 75 g (0.476 mole) of 1-bromo-3-chloropropane and 98.7 g (0.71 mole) of anhydrous potassium carbonate in 1 liter of actone was heated at reflux for 24 hr. The mixture was filtered and the filtrate was concentrated under reduced pressure to give an oil which gradually crystallized to a semi-solid. The solid was recrystallized from ethyl ether-petroleum ether (30°-60° C.) to yield 44.4 g (65%) of the title compound as a white solid, mp 36°-38° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hr
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto give an oil which
  6. customgradually crystallized to a semi-solid
  7. customThe solid was recrystallized from ethyl ether-petroleum ether (30°-60° C.)

Sources & evidence

ORD record
ord-03fbfb07a9784616ae372181a7b66452
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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