4-Nitrophenol → 2-[4-(4-Nitrophenoxy)butyl]-1H-isoindole-1,3(2H)-dione

HRID 1417309Notes

Reaction equation

HRID 1417309 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C[O-].[Na+].Br[CH2:15][CH2:16][CH2:17][CH2:18][N:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]1=[O:29]>CN(C)C=O.O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:29])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 93575N-(4-Bromobutyl)phthalimideHCID 10942334Sodium Methoxide

Product 1

HCID 161051422-[4-(4-Nitrophenoxy)butyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 14.0 g of 4-nitrophenol in 250 ml of dimethylformamide is treated with 6.0 g of sodium methoxide. After 15 minutes, 28.2 g of 2-(4-bromobutyl)-1H-isoindole-1,3(2H)-dione is added, and the mixture then stirred at room temperature for 16 hours. The reaction mixture is diluted with 1500 ml of cold water, the precipitated solid collected, washed with water, and dried. Recrystallization from ethanol gives the desired compound, m.p. 112°-114° C.

Workup

  1. customthe precipitated solid collected
  2. washwashed with water
  3. customdried
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-74a52a17b7534358912813f8275fd26b
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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