1-(Benzyloxy)-4-(3-bromopropoxy)benzene → N-[3-(4-benzyloxyphenoxy)propyl]phthalimide

HRID 2417989Notes

Reaction equation

HRID 2417989 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18]Br)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[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:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][N:24]2[C:23](=[O:25])[C:22]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]3[C:20]2=[O:30])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 111100311-(Benzyloxy)-4-(3-bromopropoxy)benzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 13338484N-[3-(4-benzyloxyphenoxy)propyl]phthalimideYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-benzyloxy-4-(3-bromopropyloxy)benzene (29.4 g) and potassium phthalimide (20.4 g) in dimethylformamide (150 ml) was stirred and heated on a steam bath for 17 hours under nitrogen. The solvent was distilled in vacuo and water (250 ml) was added to the residue. The mixture was extracted with dichloromethane and the extract dried over anhydrous potassium carbonate. The solvent was evaporated in vacuo and the residue was crystallized from ethanol-acetone to give 10.9 g (31%) of 1-benzyloxy-4-(3-phthalimidopropoxy)benzene, mp 143°-145°. A second crop which was obtained by concentrating the filtrate, weighed 9.2 g (26%), mp 137°-140°. The analysis of a sample, mp 141°-143°, from an earlier run was as follows:

Workup

  1. temperatureheated on a steam bath for 17 hours under nitrogen
  2. distillationThe solvent was distilled in vacuo and water (250 ml)
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with dichloromethane
  5. dry with materialthe extract dried over anhydrous potassium carbonate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was crystallized from ethanol-acetone

Sources & evidence

ORD record
ord-7272dadc9682469f99535dd92ecb6395
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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