Methyl 2-(2-(4-nitrophenoxy)ethoxy)acetate → HCID 59253936, compound

HRID 1957831Notes

Reaction equation

HRID 1957831 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1>C(OCC)(=O)C.[C].[Pd]>[CH3:1][O:2][C:3](=[O:18])[CH2:4][O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 59253929Methyl 2-(2-(4-nitrophenoxy)ethoxy)acetate

Product 1

HCID 59253936HCID 59253936, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

[2-(4-Nitrophenoxy)-ethoxy]acetic acid methyl ester 22 (1 g, 3.9 mmol) was dissolved in anhydrous ethyl acetate (20 ml), palladium carbon (10%, 0.1 g) added and the mixture stirred under an atmosphere of hydrogen using balloon for 30 minutes. The catalyst was filtered, the filtrate concentrated, hexane (3 ml) added, and the solid filtered to give 23 (625 mg, 70.9%) as a light brown powder. The melting point was found to be 51-52.5° C. The structure was confirmed with IR and NMR.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate concentrated
  3. additionhexane (3 ml) added
  4. filtrationthe solid filtered

Sources & evidence

ORD record
ord-6db9243217124b82a124d1563087e619
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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