3-Hydroxybenzyl alcohol → 2-{3-[3-(Hydroxymethyl)phenoxy]propyl}-1H-isoindole-1,3(2H)-dione

HRID 847748Notes

Reaction equation

HRID 847748 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[H-].[Na+].Br[CH2:13][CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26]>CS(C)=O>[OH:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH2:13][CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26]

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydride

Product 1

HCID 127800822-{3-[3-(Hydroxymethyl)phenoxy]propyl}-1H-isoindole-1,3(2H)-dioneYield 39.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 2.6 g of 3-hydroxybenzyl alcohol in 10 ml of dry dimethylsulfoxide was added dropwise with stirring under ice cooling to a suspension of 0.88 g of 60% sodium hydride in 5 ml of dry dimethylsulfoxide. After the addition, the mixture was stirred at room temperature for 20 minutes, and 6 g of N-bromopropylphthalimide was added. The mixture was reacted at room temperature for 1 hour, and ice water was added. The mixture was extracted with ether, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was crystallized with ether to afford 2.6 g of N-[3-[3-(hydroxymethyl)phenoxy]propyl]phthalimide.

Workup

  1. additionAfter the addition
  2. customThe mixture was reacted at room temperature for 1 hour
  3. extractionThe mixture was extracted with ether
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was crystallized with ether

Sources & evidence

ORD record
ord-27e6a4df3bd14b59972e1291f10c41df
Source dataset
uspto-grants-1981_10
Patent number
US04293557

Reaction notes

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