Isopropanol → 3-(Propan-2-yloxy)aniline

HRID 2274923Notes

Reaction equation

HRID 2274923 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH:9](O)([CH3:11])[CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:9]([O:8][C:4]1[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=1)([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 115683-AminophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 5732203-(Propan-2-yloxy)anilineYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-aminophenol (1.50 g, 13.8 mmol), isopropanol (3.3 g, 55 mmol), and triphenylphosphine (14.4 g, 54.9 mmol) in THF (15 mL), was added dropwise diethylazodicarboxylate (9.60 g, 55.0 mmol) over a 30 min period. The mixture was stirred at room temperature for 3 h and concentrated. The residue was diluted with water, acidified with aqueous 2N HCl and extracted with ether. The aqueous phase was basified with aqueous 2N NaOH and extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated. The resulting crude product was purified by silica gel column chromatograph (petroleum ether/EtOAc 10:1 to 5:1) to afford 3-isopropoxybenzenamine as yellow oil (1.3 g, 64%).

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with water
  3. extractionextracted with ether
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by silica gel column chromatograph (petroleum ether/EtOAc 10:1 to 5:1)

Sources & evidence

ORD record
ord-23f0111d3f324d23956c87a6ae85cb56
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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