Isobutanol → 3-(2-methylpropoxy)aniline

HRID 2274924Notes

Reaction equation

HRID 2274924 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-6af62e9a98cc4af49cb8aeb231347666
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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