{4-[(3,4-Dinitrophenyl)oxy]phenyl}methanol → HCID 57585853, compound

HRID 547610Notes

Reaction equation

HRID 547610 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=2)[CH:7]=[CH:8][C:9]=1[NH2:10]

Participants

5

Reactant 2

HCID 57585910{4-[(3,4-Dinitrophenyl)oxy]phenyl}methanolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 57585853HCID 57585853, compoundYield 108.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

{4-[(3,4-dinitrophenyl)oxy]phenyl}methanol (3.73 g, 12.9 mmol) was hydrogenated in approximately 100 ml of ethyl acetate under a balloon of hydrogen over 1.2 g of 10% Pd on carbon (wet, degussa type) for 2.5 hours. An additional 600 mg of 10% Pd on carbon (wet, degussa type) was added and the reaction was hydrogenated under a balloon of hydrogen for 14.5 hours. The catalyst was filtered away and the filtrate was concentrated. The residue was dissolved in 1:1 ethanol:ethyl acetate and hydrogenated under a balloon of hydrogen over 1.2 g of 10% Pd on carbon (wet, degussa type) for 23.5 hours to consume remaining reaction intermediates. The catalyst was filtered away and the filtrate was concentrated to give 3.21 g of crude {4-[(3,4-diaminophenyl)oxy]phenyl}methanol, which was used without further purification.

Workup

  1. filtrationThe catalyst was filtered away
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in 1:1 ethanol
  4. customto consume
  5. customreaction intermediates
  6. filtrationThe catalyst was filtered away
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a04826ac1c1f4294aa04297ab72d09d9
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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