3-Nitrobenzaldehyde → 3-Nitrobenzyl alcohol

HRID 2279210Notes

Reaction equation

HRID 2279210 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].[BH4-].[Na+]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 692673-Nitrobenzyl alcoholYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-nitrobenzaldehyde (5 g, 33.1 mmol) in MeOH (25 mL) at ambient temperature was added NaBH4 (1.25 g, 33.1 mmol) and the resulting mixture was stirred for 30 min. The reaction mixture was quenched with water. The product was extracted with CH2Cl2 thrice and the combined organic extracts were washed with H2O followed by brine, dried over Na2SO4 and concentrated under reduced pressure to furnish without purification 5 g of compound (xB). 1H NMR (CDCl3): δ 8.27 (s, 1H), 8.17 (dd, 1H), 7.73 (dd, 1H), 7.57 (t, 1H), 4.85 (s, 2H), 2.07 (s, 1H). MS (m/z): 154 [M+H]+.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionThe product was extracted with CH2Cl2 thrice
  3. washthe combined organic extracts were washed with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f090b59176624ddbb12afe5d268839ba
Source dataset
uspto-grants-2015_09
Patent number
US09133214B2

Reaction notes

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