Water → HCID 58409077, compound

HRID 2381272Notes

Reaction equation

HRID 2381272 reaction equation
[N+:1]([CH2:4][CH3:5])([O-:3])=[O:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl:14][C:15]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=1[CH:17]=[O:18].O>C(#N)C>[Cl:14][C:15]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=1[CH:17]([OH:18])[CH:4]([N+:1]([O-:3])=[O:2])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6587NitroethaneHCID 134042,4-DichlorobenzaldehydeHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 58409077HCID 58409077, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of nitroethane (8.3 g, 0.11 mol) in acetonitrile (150 ml) was added anhydrous potassium phosphate (1.0 g, 4.6 mmol) followed by 2,4-dichloro-benzaldehyde (17.5 g, 0.10 mol). The reaction mixture was stirred for 4 hours. Water (300 ml) was added and the reaction mixture was extracted with diethyl ether (200 ml). The organic extract was washed with water and dried over anhydrous Na2SO4, the solvent was removed and the resulting residue was purified by flash chromatography over silicagel (eluent:cyclohexane/ethylacetate 9:1). 20.7 g (82.5% of theory) of a threo/erythro-mixture of 1-(2,4-dichlorophenyl)-2-nitro-propan-1-ol was obtained. Crystallisation from cyclohexane yielded pure erythro 1-(2,4-dichlorophenyl)-2-nitro-propan-1-ol.

Workup

  1. extractionthe reaction mixture was extracted with diethyl ether (200 ml)
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. customthe solvent was removed
  6. customthe resulting residue was purified by flash chromatography over silicagel (eluent:cyclohexane/ethylacetate 9:1)

Sources & evidence

ORD record
ord-d9c7a90be8ad443d9e6ae93db59a3766
Source dataset
uspto-grants-2012_09
Patent number
US08258169B2

Reaction notes

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