Tetrahydrofuran → Ethyl 2-(4-aminophenoxy)acetate

HRID 507933Notes

Reaction equation

HRID 507933 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[CH3:2].O1CCCC1.[H][H]>[C].[Pd].C(O)C>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 308938Ethyl 2-(4-nitrophenoxy)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 412616Ethyl 2-(4-aminophenoxy)acetateYield 74%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Ethyl(4-nitrophenoxy)acetate (10.0 g, 44.4 mmol) and 10% palladium-carbon (50% water-containing product, 3.0 g) were added to a mixed solution of tetrahydrofuran (50 mL) and ethanol (50 mL), and the mixture was stirred at room temperature for 18 hr in a hydrogen stream. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:2-2:3-1:1), and the obtained crystals were recrystallized from ethyl acetate-hexane to give the title compound (6.4 g, yield 74%) as pale-pink prism crystals.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6a76f5d34475470ca636823c2493d7a1
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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