HCID 15724711, compound → 2-{3-[3-(Hydroxymethyl)phenoxy]propyl}-1H-isoindole-1,3(2H)-dione

HRID 704915Notes

Reaction equation

HRID 704915 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9][OH:10].[K].[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[OH:10][CH2:9][C:8]1[CH:7]=[C:6]([CH:13]=[CH:12][CH:11]=1)[O:5][CH2:4][CH2:3][CH2:2][N:19]1[C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]2[C:15]1=[O:25]

Participants

5

Reactant 2

HCID 15724711HCID 15724711, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 127800822-{3-[3-(Hydroxymethyl)phenoxy]propyl}-1H-isoindole-1,3(2H)-dioneYield 76.9%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6342AcetonitrileSolvent

Procedure

m-(3-Chloropropyloxy)benzyl alcohol (14 g), phthalimide potassium salt (13 g) and tetra-n-butyl ammonium hydrogen sulfate (2 g) were suspended in 200 g of acetonitrile. The suspension was refluxed for 18 hours. After cooling, the insoluble matter was removed by filtration, and the filtrate was concentrated. The concentrate was taken into ethyl acetate, washed with a 1N aqueous solution of sodium hydroxide and water, and then dried. The solvent was evaporated, and the residue was recrystallized from ethanol to give 16.7 g (yield 76.9%) of N-[3-(3-hydroxymethylphenoxy)propyl]phthalimide.

Workup

  1. temperatureThe suspension was refluxed for 18 hours
  2. temperatureAfter cooling
  3. customthe insoluble matter was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. washwashed with a 1N aqueous solution of sodium hydroxide and water
  6. customdried
  7. customThe solvent was evaporated
  8. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-ba6a309b581d42a999ba4fe73b55b587
Source dataset
uspto-grants-1991_01
Patent number
US04988828

Reaction notes

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