3-Nitrophenylacetic acid → 3-Nitrophenylethyl alcohol

HRID 1256105Notes

Reaction equation

HRID 1256105 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11](O)=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].B.C1COCC1>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][OH:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 158763-Nitrophenylacetic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 1040583-Nitrophenylethyl alcoholYield 53.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-nitrophenyl)acetic acid (1.8 g, 0.01 mol) in THF (20 ml) at 0° C., was added BH3THF dropwise (1 M, 22 ml, 0.022 mol), removed ice bath and stirred at room temperature over night. The reaction was quenched with water and extracted with EtOAc, washed with water and brine, dried over Na2SO4. Concentrated to get crude 2-(3-nitrophenyl)ethanol as light yellow solid (0.9 g).

Workup

  1. customremoved ice bath
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationConcentrated

Sources & evidence

ORD record
ord-c7b86bd1352c4806bafb80c8c95fe0af
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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