1-Benzyloxy-4-[3-(1-methylethyl)aminopropoxy]benzene → 4-[3-(1-Methylethyl)aminopropoxy]phenol

HRID 2417994Notes

Reaction equation

HRID 2417994 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][NH:19][CH:20]([CH3:22])[CH3:21])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)C>[CH3:22][CH:20]([NH:19][CH2:18][CH2:17][CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1)[CH3:21]

Participants

4

Reactant 1

HCID 133384801-Benzyloxy-4-[3-(1-methylethyl)aminopropoxy]benzene

Product 1

HCID 133384864-[3-(1-Methylethyl)aminopropoxy]phenolYield 100.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-Benzyloxy-4-[3-(1-methylethyl)aminopropoxy]benzene (11.5 g) was added to an hydrogenation bottle containing 250 ml of ethanol and hydrogenated over 1 g of 10% palladium on carbon (room temperature; starting pressure of 50 psi). After the theoretical uptake of hydrogen, the mixture was filtered and the solvent distilled in vacuo giving 8.1 g of 4-[3-(1-methylethyl)aminopropoxy]phenol, mp 92°-100° (96.4% pure by gas chromatography). Mass spectrum was compatible.

Workup

  1. filtrationAfter the theoretical uptake of hydrogen, the mixture was filtered
  2. distillationthe solvent distilled in vacuo

Sources & evidence

ORD record
ord-ee67489265104111977ecff667a4e53b
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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