Isopropanol → 4-Benzyloxy-2,6-bis(trifluoromethyl)aniline

HRID 1373734Notes

Reaction equation

HRID 1373734 reaction equation
C(O)(C)C.[CH2:5]([O:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[C:16]([N+:23]([O-])=O)=[C:15]([C:26]([F:29])([F:28])[F:27])[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH2:5]([O:12][C:13]1[CH:14]=[C:15]([C:26]([F:27])([F:28])[F:29])[C:16]([NH2:23])=[C:17]([C:19]([F:20])([F:21])[F:22])[CH:18]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24489Sodium Dithionite2×HCID 210756014-Benzyloxy-2,6-bis(trifluoromethyl)nitrobenzene

Product 1

HCID 210756004-Benzyloxy-2,6-bis(trifluoromethyl)anilineYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

Isopropanol (450 mL) was added to 4-benzyloxy-2,6-bis(trifluoromethyl)nitrobenzene (9.00 g, 24.6 mmol) and the latter was dissolved in the former by heating at 70° C. A solution of sodium dithionite (14.1 g, 81.2 mmol) in water (150 mL) was added dropwise to the resulting solution. After stirring for 30 minutes at the same temperature, a solution of sodium dithionite (7.28 g, 41.8 mmol) in water (150 mL) was added further. The reaction mixture was stirred at the same temperature for 14 hours and then, the isopropanol was distilled off under reduced pressure. Ethyl acetate was added to the resulting suspension to separate it into layers. The aqueous layer was extracted with ethyl acetate twice. The organic layers were combined, washed successively with water and saturated saline, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent, whereby 8.26 g (yield: 100%) of 4-benzyloxy-2,6-bis(trifluoromethyl)aniline was obtained as colorless needle-like crystals.

Workup

  1. dissolutionthe latter was dissolved in the former
  2. stirringThe reaction mixture was stirred at the same temperature for 14 hours
  3. distillationthe isopropanol was distilled off under reduced pressure
  4. additionEthyl acetate was added to the resulting suspension
  5. customto separate it into layers
  6. extractionThe aqueous layer was extracted with ethyl acetate twice
  7. washwashed successively with water and saturated saline
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationdistilled under reduced pressure
  10. customto remove the solvent

Sources & evidence

ORD record
ord-3c3e07e94623493eaa23bbb02d062996
Source dataset
uspto-grants-2007_01
Patent number
US07163944B2

Reaction notes

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