Hexane → 4-[(2-Methoxyethoxy)methoxy]aniline

HRID 1603241Notes

Reaction equation

HRID 1603241 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1.C([O-])=O.[NH4+].CCCCCC>C(O)C.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 2723923Ammonium formateHCID 196090861-[(2-methoxyethoxy)methoxy]-4-nitroBenzene

Product 1

HCID 131356894-[(2-Methoxyethoxy)methoxy]anilineYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of 200 mg (0.88 mmol) of 1-[(2-methoxyethoxy) methoxy]-4-nitrobenzene (21), 100 mg of 10% Pd/C and 550 mg (8.7 mmol) of ammonium formate in 10 mL of absolute ethanol was stirred at room temperature for 18 hours. The reaction mixture was diluted with 100 mL of absolute ethanol and passed through a small pad of celite. The filtrate was concentrated and purified by silica gel column chromatography using 8:2 ethyl acetate:hexane as the eluent to yield 130 mg (0.65 mmol, 75%) of 4-[(2-methoxyethoxy)methoxy]benzenamine (22). NMR, IR and MS data confirmed compound identity.

Workup

  1. concentrationThe filtrate was concentrated
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-b72cad446df04ae38b4f6c628012200f
Source dataset
uspto-grants-1999_11
Patent number
US05986094

Reaction notes

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