Sulfuric Acid → 1-(2-Aminophenyl)-3,3-dimethylbutan-2-ol

HRID 656802Notes

Reaction equation

HRID 656802 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[CH:3]([OH:14])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O.S(=O)(=O)(O)O.[H][H]>C1COCC1.[Pd]>[NH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][CH:3]([OH:14])[C:2]([CH3:15])([CH3:1])[CH3:16]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 592538163,3-Dimethyl-1-(2-nitrophenyl)butan-2-olHCID 178418361HCID 178418361, compound

Product 1

HCID 592538141-(2-Aminophenyl)-3,3-dimethylbutan-2-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3 g (13.4 mmol) of 3,3-dimethyl-1-(2-nitrophenyl)butan-2-ol are stirred in 50 ml of THF with 2.06 g of 65 percent sulfuric acid and 0.214 g of palladium/carbon (10%) at 90° C. under 10 bar of hydrogen pressure for 16 hours. Subsequently, the solution is filtered with suction through Celite and the filtrate is concentrated by rotary evaporation. After dissolution in ethyl acetate, washing with saturated sodium bicarbonate solution, and removal and concentration of the organic phase under reduced pressure, 2.2 g (75% of theory) of a solid are obtained. Purity (GC-MS): 88%.

Workup

  1. filtrationSubsequently, the solution is filtered with suction through Celite
  2. concentrationthe filtrate is concentrated by rotary evaporation
  3. dissolutionAfter dissolution in ethyl acetate
  4. washwashing with saturated sodium bicarbonate solution, and removal and concentration of the organic phase under reduced pressure, 2.2 g (75% of theory) of a solid
  5. customare obtained

Sources & evidence

ORD record
ord-bd8bda76c26a4802bc5c4fc0443e5398
Source dataset
uspto-grants-2011_12
Patent number
US08071824B2

Reaction notes

Loading…