Water → Phthalimide

HRID 974024Notes

Reaction equation

HRID 974024 reaction equation
BrCCCC[N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].C1(C2C=CC(O)=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:10]1(=[O:11])[NH:6][C:7](=[O:16])[C:8]2=[CH:15][CH:14]=[CH:13][CH:12]=[C:9]12

Participants

6

Reactant 4

HCID 962WaterHCID 71034-HydroxybiphenylHCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimide

Product 1

HCID 6809PhthalimideYield 162.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of N-(4-bromobutyl)phthalimide (14.1 g, 50 mmol), 4-phenylphenol (8.5 g, 50 mmol), and potassium carbonate (15.0 g, 108 mmol) in DMF (75 ml) was stirred under nitrogen for 16 hours at 85° C., then water (200 ml) was added dropwise to the cooled solution. The precipitate was collected by filtration, and recrystallized from methanol-water to provide N-[4-(1,1'-bi-phenyl]-4-yloxy)butyl]phthalimide as an off-white solid (11.94 g, 64% yield), mp 114°-115° C.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-2c64b742db1f4ba2a73a18f98e46e28e
Source dataset
uspto-grants-1991_11
Patent number
US05066658

Reaction notes

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