Water → 2-(2,4-Dinitrophenyl)ethanol

HRID 1042614Notes

Reaction equation

HRID 1042614 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.CCCCCC>O1CCCC1>[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 962WaterHCID 8058HexaneHCID 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) 2,4-dinitrophenylacetic acid are dissolved in 150 ml tetrahydrofuran and added dropwise in a the course of 2 hours to 300 ml (300 mmol) of a borane-tetrahydrofuran complex 1.0 M solution in tetrahydrofuran. After 3 hours at 25° C., 200 ml water are carefully added. The reaction mixture is then partitioned between ethyl acetate and water; the organic phase was washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 400 g silica gel using toluene:ethyl acetate 1:1 as eluant and crystallization form ethylacetate:hexane mixture to yield 20.7 g (98%) of 2-(2,4-dinitrophenyl)ethanol as yellowish crystals.

Workup

  1. customThe reaction mixture is then partitioned between ethyl acetate and water
  2. washthe organic phase was washed repeatedly with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customcrystallization
  7. customform ethylacetate

Sources & evidence

ORD record
ord-31e81d2c1f974e318f190afb7a751902
Source dataset
uspto-grants-2013_10
Patent number
US08557922B2

Reaction notes

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