N-[3-(4-benzyloxyphenoxy)propyl]phthalimide → 4-(3-Phthalimidopropoxy)phenol

HRID 2417999Notes

Reaction equation

HRID 2417999 reaction equation
[H][H].C([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][N:21]2[C:25](=[O:26])[C:24]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])=[CH:13][CH:12]=1)C1C=CC=CC=1>[Pd].C(O)(=O)C>[C:22]1(=[O:31])[N:21]([CH2:20][CH2:19][CH2:18][O:17][C:14]2[CH:15]=[CH:16][C:11]([OH:10])=[CH:12][CH:13]=2)[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]12

Participants

5

Reactant 2

HCID 13338484N-[3-(4-benzyloxyphenoxy)propyl]phthalimideHCID 178418361HCID 178418361, compound

Product 1

HCID 133384944-(3-Phthalimidopropoxy)phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a hydrogen bottle containing 0.5 g of 10% palladium on carbon and acetic acid (250 ml) was added the above 1-benzyloxy-4-(3-phthalimidopropoxy)benzene (16 g). The mixture was shaken at 50° in the Parr hydrogenation apparatus for about 4 hours and cooled to room temperature. The mixture was filtered and the solvent distilled in vacuo. The residue was crystallized from toluene to yield 10.8 g (88%), mp 135°-7° of 4-(3-phthalimidopropoxy)phenol.

Workup

  1. filtrationThe mixture was filtered
  2. distillationthe solvent distilled in vacuo
  3. customThe residue was crystallized from toluene

Sources & evidence

ORD record
ord-14194f1efff94ecdae047780e9ffe6c7
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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