Acetic Acid → 2-t-Butyl-5-(t-butyldimethylsilyloxymethyl)aniline

HRID 1418178Notes

Reaction equation

HRID 1418178 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])=[CH:7][C:6]=1[N+:20]([O-])=O)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>CO.[Zn]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15])=[CH:7][C:6]=1[NH2:20])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 193484482-t-Butyl-5-(t-butyldimethylsilyloxymethyl)-1-nitrobenzene

Product 1

HCID 193487032-t-Butyl-5-(t-butyldimethylsilyloxymethyl)aniline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

81 g (1.24 mol) of zinc powder were added to a solution of 25.19 g (77.9 mmol) of 2-t-butyl-5-(t-butyldimethylsilyloxymethyl)-1-nitrobenzene (prepared as described in Preparation 11) in 270 ml of methanol, and then 10.8 ml of acetic acid were added to the resulting mixture, with ice-cooling. After the exothermic reaction had subsided, the reaction mixture was heated under reflux for 3 hours and then allowed to cool to room temperature, after which it was filtered using a Celite (trade mark) filter aid, and the zinc used was washed with methanol. The filtrate was combined with the washings and the combined mixture was concentrated by evaporation under reduced pressure. The concentrate was dissolved in ethyl acetate, and the resulting solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, to give 22.9 g (a quantitative yield) of the title compound as an oily substance. The compound could be used without purification.

Workup

  1. temperaturecooling
  2. customAfter the exothermic reaction
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for 3 hours
  5. filtrationafter which it was filtered
  6. filtrationfilter aid
  7. washthe zinc used was washed with methanol
  8. concentrationthe combined mixture was concentrated by evaporation under reduced pressure
  9. dissolutionThe concentrate was dissolved in ethyl acetate
  10. washthe resulting solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  11. dry with materialafter which it was dried over anhydrous sodium sulfate
  12. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-8270928d231542a093d420e45be23bb6
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

Loading…