3,5-Dinitrobenzoic acid → 3,5-Dinitrobenzyl alcohol

HRID 2303988Notes

Reaction equation

HRID 2303988 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2].B.O1CCCC1>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[CH2:7][OH:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74333,5-Dinitrobenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 1169783,5-Dinitrobenzyl alcoholYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3,5-dinitrobenzoic acid (213.0 g, 1.00 mol) in anhydrous THF (1500 mL) at 0° C. was added borane-tetrahydrofuran complex (1.5 L of 1M in THF, 1.50 mol) over 1 h. The resulting heterogeneous mixture was stirred at 0° C. for 3 h and at 25° C. for 18 h. The resulting homogeneous solution was quenched with H2O and concentrated in vacuo until solids were present. The solids were filtered, washed with H2O and dissolved in EtOAc. The aqueous filtrate was extracted with EtOAc. The combined organics were washed with aqueous NaHCO3 and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford 176.0 g (89%) of the sub-title compound as a solid which was used without further purification.

Workup

  1. customThe resulting homogeneous solution was quenched with H2O
  2. concentrationconcentrated in vacuo until solids
  3. filtrationThe solids were filtered
  4. washwashed with H2O
  5. dissolutiondissolved in EtOAc
  6. extractionThe aqueous filtrate was extracted with EtOAc
  7. washThe combined organics were washed with aqueous NaHCO3 and brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-688d6414f1b3448e9698b596da3fdc3c
Source dataset
uspto-grants-2002_08
Patent number
US06433186B1

Reaction notes

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