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

HRID 1193652Notes

Reaction equation

HRID 1193652 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-5fc14b69f2cf4e82b434f8b3c23df8ee
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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