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

HRID 1709829Notes

Reaction equation

HRID 1709829 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+]>CC(C)=O>[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

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 50 g (0.238 mole) of ethyl homovanillate, 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 acetone 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 white solid, m.p. 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-06e28c5c31bd4e2e8627dcdc5fb785d3
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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