2-Nitrotoluene → HCID 59253815, compound

HRID 656798Notes

Reaction equation

HRID 656798 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])([O-:3])=[O:2].[OH-].[K+].[CH2:13]1[CH:15]([CH:16]([OH:19])C#N)[CH2:14]1>CN(C=O)C>[CH:15]1([CH:16]([OH:19])[CH2:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 69442-NitrotolueneHCID 14797Potassium HydroxideHCID 113893592-Cyclopropyl-2-hydroxyacetonitrile2×

Product 1

HCID 59253815HCID 59253815, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4.9 g (35.7 mmol) of 2-nitrotoluene in 30 ml of DMF are added, within one hour, 0.168 g (2.55 mmol; 85% purity) of KOH and simultaneously 5 g (71.34 mmol) of cyclopropylcarboxaldehyde. The mixture is stirred at room temperature (RT) for 0.5 h, then 0.5 equivalent of cyclopropylcarboxaldehyde is added and the mixture is stirred at RT for a further hour. Subsequently, a majority of the DMF is distilled off under reduced pressure, and the residue is admixed with water and extracted with ethyl acetate. After the evaporation of the solvent and chromatography using silica gel (elution with toluene/ethyl acetate mixtures), 4.2 g (yield 55% of theory, purity (GC-MS 95.9%) of 1-cyclopropyl-2-(2-nitrophenyl)ethanol were obtained in the form of an oil.

Workup

  1. stirringthe mixture is stirred at RT for a further hour
  2. distillationSubsequently, a majority of the DMF is distilled off under reduced pressure
  3. extractionextracted with ethyl acetate
  4. customAfter the evaporation of the solvent and chromatography

Sources & evidence

ORD record
ord-30dc0444c6bb4bdea64111126728ec4f
Source dataset
uspto-grants-2011_12
Patent number
US08071824B2

Reaction notes

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