Water → 2-(2,4-Dinitrophenyl)ethanol

HRID 523323

Reaction equation

HRID 523323 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][C:14](O)=[O:15])([O-:3])=[O:2].O.C(OCC)(=O)C>C1COCC1>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][CH2:14][OH:15])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 8857Ethyl AcetateHCID 2215132,4-Dinitrophenylacetic acid

Product 1

HCID 118307342-(2,4-Dinitrophenyl)ethanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

22.6 g (100 mmol) of 2,4-dinitrophenylacetic acid are dissolved in 150 mL of THF and added dropwise in 2 hours to 300 mL of a borane-THF complex 1.0 M solution in THF. After 3 hours at 25° C., 200 ml of water are added. The reaction mixture is then poured to ethyl acetate and water. The organic phase is washed repeatedly with water and dried over sodium sulphate, filtered and concentrated under pressure. Chromatography of the residue using toluene: ethylacetate 1:1 as eluant and crystallization in ethylacetate/hexane yielded to 20.7 g (98%) of 2-(2,4-dinitrophenyl)ethanol as yellowish crystal

Workup

  1. washThe organic phase is washed repeatedly with water
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under pressure
  5. customcrystallization in ethylacetate/hexane

Sources & evidence

ORD record
ord-3a03fd65b37444878f532bf014cb9422
Source dataset
uspto-grants-2016_05
Patent number
US09334366B2

Linked notes

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