Sodium Hydroxide → 2-(2-Amino-phenoxy)-ethanol

HRID 1954662Notes

Reaction equation

HRID 1954662 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O.Cl[Sn]Cl.[Sn].[OH-].[Na+]>Cl.O>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 27370592-(2-nitrophenoxy)ethanolHCID 5352426Tin atom

Product 1

HCID 125388802-(2-Amino-phenoxy)-ethanolYield 80.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

8.9 g (48.59 mmol) 2-(2-hydroxyethoxy)nitrobenzene A2, 16.44 g (72.88 mmol) SnCl2. 2H2O and 17.3 g (145.77 mmol) tin were stirred in 30.84 ml aqueous HCl (30%) and 25 ml water at 90° C. for 8 hours. After cooling, the solution was treated with aqueous 5n sodium hydroxide solution and stirred for 3 hours at 90° C. The aqueous solution was subsequently decanted, wherein, upon cooling, the crude product crystallized out and was removed by suction. This crude product was then taken up in methanol, warmed and the suspension was filtered. The filtrate was then concentrated in vacuo. 6 g of light-brown crystals were obtained; yield 80%.

Workup

  1. temperatureAfter cooling
  2. customThe aqueous solution was subsequently decanted
  3. temperaturewherein, upon cooling
  4. customthe crude product crystallized out
  5. customwas removed by suction
  6. temperaturewarmed
  7. filtrationthe suspension was filtered
  8. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-a72711845d1344cf888d5e64c5a6d13f
Source dataset
uspto-grants-2000_09
Patent number
US06124135

Reaction notes

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