1-(Chloromethyl)-4-(4-phenylbutoxy)benzene → N-[p-(4-phenylbutoxy)benzyl]phthalimide

HRID 704370Notes

Reaction equation

HRID 704370 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=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.C(OCC)(=O)C>[C:14]1([CH2:13][CH2:12][CH2:11][CH2:10][O:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:24]3[C:23](=[O:25])[C:22]4=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]4[C:20]3=[O:30])=[CH:4][CH:5]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 151155321-(Chloromethyl)-4-(4-phenylbutoxy)benzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 14881544N-[p-(4-phenylbutoxy)benzyl]phthalimideYield 109.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.20 g of p-chloromethyl-(4-phenylbutoxy)benzene and 1.15 g of potassium phthalimide in 20 ml of N,N-dimethylformamide was stirred at 100° C. for 3 hours. The reaction mixture was diluted with ethyl acetate, and the dilution was washed with three portions of water and then with saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residual solid was recrystallized from ethyl acetate to give 1.85 g of N-[p-(4-phenylbutoxy)benzyl]phthalimide. Melting point 106°-107.5° C. ##STR32##

Workup

  1. washthe dilution was washed with three portions of water
  2. dry with materialwith saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residual solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a4b2c6320646427a978917fb0471796d
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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