5-(Methoxymethyl)-2-nitrophenol → HCID 23112756, compound

HRID 1764937Notes

Reaction equation

HRID 1764937 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([N+:11]([O-])=O)=[C:8]([OH:10])[CH:9]=1.[H][H]>CCO.O=[Pt]=O>[NH2:11][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][O:2][CH3:1])=[CH:9][C:8]=1[OH:10]

Participants

5

Reactant 2

HCID 211061855-(Methoxymethyl)-2-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 23112756HCID 23112756, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 2 (20 g, 108 mmol) in EtOH (300 mL) was hydrogenated over PtO2 (300 mg) in Parr pressure apparatus until the theoretical amount of hydrogen was absorbed. The catalyst was removed by filtration through a pad of Celite, and the filtrate was concentrated in vacuo to a solid (21 g, 100%). This solid was combined with material obtained from a smaller run then passed through a pad of silica gel (500 g) eluted with ether. Fractions containing pure product were combined, dried then concentrates, yield 20 g (89%) m.p. 108–108.5° C. (uncorrected).

Workup

  1. customwas absorbed
  2. customThe catalyst was removed by filtration through a pad of Celite
  3. concentrationthe filtrate was concentrated in vacuo to a solid (21 g, 100%)
  4. customobtained from a smaller run
  5. washeluted with ether
  6. additionFractions containing pure product
  7. customdried

Sources & evidence

ORD record
ord-b4c0d668a46a496aa784030fe4dd5c6f
Source dataset
uspto-grants-2007_06
Patent number
US07226487B2

Reaction notes

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