Methanol → 2-(4-Aminophenoxy)ethanol

HRID 28608

Reaction equation

HRID 28608 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:5]=1)([O-])=O.CO.[H][H]>[Pd].C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][OH:11])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 853812-(4-Nitrophenoxy)ethanolHCID 178418361HCID 178418361, compound

Product 1

HCID 808922-(4-Aminophenoxy)ethanolYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(4-nitro-phenoxy)-ethanol (1.0 g, 5.5 mmol), 10% palladium on carbon (110 mg), methanol (40 ml), and ethyl acetate (20 ml) was treated with hydrogen gas (50 psi) on a Parr shaker for 1 hour. The mixture was filtered through a pad of celite under suction and the filtrate was concentrated under reduced pressure to give 2-(4-amino-phenoxy)-ethanol (820 mg, 99% yield). 1H NMR (DMSO-d6) δ 3.61-3.64 (m, 2H, CH2), 3.80 (t, 2H, J=5.0 Hz CH2), 4.57 (br s, 2H, NH2), 4.74 (t, 1H, J=5.6 Hz, OH), 6.47 (d, 2H, J=8.7 Hz, Ar), 6.62 (d, 2H, J=8.8 Hz, Ar).

Workup

  1. filtrationThe mixture was filtered through a pad of celite under suction
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c14b0b37e418444eaf2c2344f16da694
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

Loading…