Acetone → 2-(Isopropylamino)phenol

HRID 1782551Notes

Reaction equation

HRID 1782551 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH3:9][C:10]([CH3:12])=O.[O-]S([O-])(=O)=O.[Mg+2]>[Pd]>[CH:10]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8])([CH3:12])[CH3:9]

Participants

5

Reactant 3

HCID 180AcetoneHCID 58012-AminophenolHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 5860122-(Isopropylamino)phenol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
100 °C

Procedure

Into a 300 mL autoclave were charged 12 g (109.92 mmol) of o-aminophenol, 100 mL (79 g; 1.4 mol) of acetone, 0.6 g of Pd/C (Pd content: 5% by mass) and 30 g of MgSO4, and the contents of the autoclave were heated at 100° C. while stirring under a hydrogen pressure of 1.0 MPa. After the elapse of 1 h, the hydrogen absorption was ceased, and the reaction was terminated. The resultant reaction solution was subjected to suction filtration to remove Pd/C and MgSO4 therefrom, and the filtrate thus separated was concentrated and then mixed with water to crystallize a reaction product. The thus obtained reaction product was dried to obtain 2-(isopropylamino)phenol. As a result, it was confirmed that the yield of 2-(isopropylamino)phenol was 93%, and the oxygen absorption initiation time as an index of determining an oxidation-inhibiting property thereof was 370 min.

Workup

  1. customAfter the elapse of 1 h, the hydrogen absorption
  2. customthe reaction was terminated
  3. customThe resultant reaction solution
  4. filtrationwas subjected to suction filtration
  5. customto remove Pd/C and MgSO4
  6. customthe filtrate thus separated
  7. concentrationwas concentrated
  8. additionmixed with water
  9. customto crystallize a reaction product
  10. customThe thus obtained reaction product
  11. customwas dried

Sources & evidence

ORD record
ord-a66bff23406847e9a3334b516b0044ad
Source dataset
uspto-grants-2009_03
Patent number
US07498467B2

Reaction notes

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