Isobutanol → 3-(2-methylpropoxy)aniline

HRID 2281263Notes

Reaction equation

HRID 2281263 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH3:9][CH:10]([CH3:13])[CH2:11]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:9]([O:8][C:4]1[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=1)[CH:10]([CH3:13])[CH3:11]

Participants

6

Reactant 4

HCID 6560IsobutanolHCID 115683-AminophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 64866083-(2-methylpropoxy)anilineYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-aminophenol (500 mg, 4.60 mmol), 2-methylpropan-1-ol (1.40 g, 18.9 mmol) and triphenylphosphine (4.80 g, 16.2 mmol) in THF (10 mL) was added dropwise diethylazodicarboxylate (3.20 g, 18.3 mmol) over a 30 min period. The mixture was stirred at room temperature for 3 h. The solvent was evaporated and 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 15:1) to afford 3-isobutoxybenzenamine as yellow oil (330 mg, 45%).

Workup

  1. customThe solvent was evaporated
  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 15:1)

Sources & evidence

ORD record
ord-ddc4506c8be445b6aefd6dc154ccdc7e
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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