HCID 20446928, compound → 4-[5-(1-Methylethyl)aminopentoxy]phenol

HRID 2417995Notes

Reaction equation

HRID 2417995 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2C=[C:20]([NH:22][CH:23]([CH3:25])[CH3:24])[CH:19]=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd]>[CH3:25][CH:23]([NH:22][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1)[CH3:24]

Participants

5

Reactant 2

HCID 20446928HCID 20446928, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 133384884-[5-(1-Methylethyl)aminopentoxy]phenolYield 76.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1-benzyloxy-4-[5-(1-methylethyl)aminophenoxy]benzene (24 g) in acetic acid (250 ml) was hydrogenated over 1 g 10% palladium on carbon. After shaking for 0.5 hours at room temperature, the theoretical amount of hydrogen was taken up. The solvent was removed by distillation in vacuo and the residue dissolved in water. The solution was basified with saturated sodium bicarbonate solution and the product was recovered by filtration to give 13.0 g (75%) of 4-[5-(1-methylethyl)aminopentoxy]phenol, mp 95°-99° (95.7% pure by gas chromatography). Mass spectrum was compatible with the expected product.

Workup

  1. customThe solvent was removed by distillation in vacuo
  2. dissolutionthe residue dissolved in water
  3. filtrationthe product was recovered by filtration

Sources & evidence

ORD record
ord-dd80e40835864255a0bab407d7f2a48c
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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