3-Methyl-2-nitrophenylacetic acid → 2-(3-Methyl-2-nitrophenyl)ethan-1-ol

HRID 2211882Notes

Reaction equation

HRID 2211882 reaction equation
[CH3:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH2:8][C:9](O)=[O:10])[CH:5]=[CH:6][CH:7]=1>C1COCC1>[CH3:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][CH2:9][OH:10]

Participants

3

Reactant 1

HCID 137789363-Methyl-2-nitrophenylacetic acid

Product 1

HCID 136636522-(3-Methyl-2-nitrophenyl)ethan-1-olYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A round bottomed flask was charged with 1.2 g (6 mmol) 3-methyl-2-nitro-phenylacetic acid and 24 mL anhydrous THF. The reaction was cooled to 0° C. and then treated with 4.0 mL 2M BH3-DMS in THF (7.8 mmol) over 5 m. The reaction was allowed to warm to rt overnight. The volatile solvents were removed in vacuo and the resulting material was partitioned between EtOAc/1 M NaHCO3. The organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give 1.06 g (95% yield) as a light, orange oil. 1H NMR (400 MHz, CDCl3) δ 7.32–7.16 (m, 3H), 3.84 (t, J=6.4 Hz, 2H), 2.81 (t, J=6.4 Hz, 2H), 2.30 (s, 3H).

Workup

  1. temperatureto warm to rt overnight
  2. customThe volatile solvents were removed in vacuo
  3. customthe resulting material was partitioned between EtOAc/1 M NaHCO3
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give 1.06 g (95% yield) as a light, orange oil

Sources & evidence

ORD record
ord-50a906062b0147c7a1c960f496d61b68
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

Loading…