4-(3-Chloropropoxy)-3-methoxybenzeneacetic acid ethyl ester → 4-[3-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)propoxy]-3-methoxybenzeneacetic acid ethyl ester

HRID 346239Notes

Reaction equation

HRID 346239 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15]Cl)=[C:8]([O:17][CH3:18])[CH:7]=1)[CH3:2].[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[K]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][N:24]2[C:20](=[O:30])[C:21]3[C:22](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:23]2=[O:25])=[C:8]([O:17][CH3:18])[CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 144071784-(3-Chloropropoxy)-3-methoxybenzeneacetic acid ethyl esterHCID 24194345Phthalimide potassium salt

Product 1

HCID 679304314-[3-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)propoxy]-3-methoxybenzeneacetic acid ethyl esterYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 40.5 g (0.141 mole) of 4-(3-chloropropoxy)-3-methoxybenzeneacetic acid ethyl ester and 27.2 g (0.144 mole) of potassium phthalimide (98%, Aldrich) in 300 mL of dimethylformamide was stirred and heated at reflux for 5 h, then was stirred at ambient temperature overnight. The solvent was evaporated under reduced pressure to give 52.3 g (93%) of a gummy residue which solidified upon standing. An analytical sample, mp 70°-72° C., was prepared from ethyl ether-petroleum ether (30°-60° C.) as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 h
  3. stirringwas stirred at ambient temperature overnight
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8c4a201477fd4565928504bdcf802fd1
Source dataset
uspto-grants-1991_10
Patent number
US05061720

Reaction notes

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