Isopropanol → 3-Methoxy-5-(propan-2-yloxy)aniline

HRID 881988Notes

Reaction equation

HRID 881988 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](O)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:30][CH:31]([OH:33])[CH3:32]>C1COCC1.C(OCC)(=O)C>[CH:31]([O:33][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([O:8][CH3:9])[CH:5]=1)[NH2:1])([CH3:32])[CH3:30]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 119535163-Amino-5-methoxyphenol

Product 1

HCID 115719053-Methoxy-5-(propan-2-yloxy)anilineYield 93.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-amino-5-methoxyphenol (Example 20, step i, 140 mg, 1.0 mmol), triphenylphosphine (390 mg, 1.5 mmol) and propan-2-ol (90 ul, 1.2 mmol) in THF (3 ml) was added portion wise di-tert-butyl diazocarboxylate (345 mg, 1.5 mmol) at room temperature. After stirring for 3 hours the reaction mixture was diluted with ethyl acetate and extracted with a 1N aqueous solution of HCl. The combined aqueous phases were brought to pH=10 with a aqueous solution of 1N NaOH and then extracted with ethyl acetate. The combined organics were filtered through a hydrophobic frit and the solvents were removed under reduced pressure to give 3-isopropoxy-5-methoxyaniline as a light brown oil (169 mg).

Workup

  1. extractionextracted with a 1N aqueous solution of HCl
  2. extractionextracted with ethyl acetate
  3. filtrationThe combined organics were filtered through a hydrophobic frit
  4. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-58b73a99c15e4b96b20d996c778f9ae1
Source dataset
uspto-grants-2015_03
Patent number
US08993757B2

Reaction notes

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