2-(4-Methoxy-2-nitrophenyl)acetic acid → 2-(4-Methoxy-2-nitrophenyl)ethan-1-ol

HRID 1914691Notes

Reaction equation

HRID 1914691 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](O)=[O:11])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1

Participants

3

Reactant 1

HCID 114131802-(4-Methoxy-2-nitrophenyl)acetic acid

Product 1

HCID 198355352-(4-Methoxy-2-nitrophenyl)ethan-1-olYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-methoxy-2-nitrophenyl)acetic acid (400 mg; 1.9 mmol; 1 eq) in THF (10 mL) at 0° C. is added slowly under nitrogen borane-tetrahydrofuran complex (4.74 mL; 1 M; 4.7 mmol; 2.5 eq) and the reaction is stirred overnight at room temperature. No conversion is observed. The reaction mixture is heated at 70° C. for 2 h. The reaction is quenched by addition of water and the expected product is extracted with EtOAc. The organic phase is dried over MgSO4 and the solvent removed under reduced pressure. The residue obtained is purified by the flash chromatography using cyclohexane/EtOAc (7/3) as eluent to afford 350 mg (94%) of the title compound as a yellow oil. 1H NMR (CDCl3) δ 7.20 (d, J=3.0 Hz, 1H), 7.06 (d, J=8.0 Hz, 1H), 6.85 (dd, J=8.0, 3.0 Hz, 1H), 3.66 (t, J=9.0 Hz, 2H), 3.61 (s, 3H), 2.86 (t, J=9.0 Hz, 2H), 1.88 (br s, 1H). HPLC (max plot) 100%; Rt 2.48 min.

Workup

  1. temperatureThe reaction mixture is heated at 70° C. for 2 h
  2. customThe reaction is quenched by addition of water
  3. extractionthe expected product is extracted with EtOAc
  4. dry with materialThe organic phase is dried over MgSO4
  5. customthe solvent removed under reduced pressure
  6. customThe residue obtained
  7. customis purified by the flash chromatography

Sources & evidence

ORD record
ord-30011162150b4012ad75e34acfb79ea2
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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