Ethyl Acetate → HCID 14404121, compound

HRID 465507Notes

Reaction equation

HRID 465507 reaction equation
[OH:1][CH:2]([C:4]1[CH:5]=[C:6]([S:10]([CH2:13][N+:14]([O-:16])=[O:15])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)[CH3:3].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(OCC)(=O)C>ClCCl>[C:2]([C:4]1[CH:5]=[C:6]([S:10]([CH2:13][N+:14]([O-:16])=[O:15])(=[O:11])=[O:12])[CH:7]=[CH:8][CH:9]=1)(=[O:1])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 19875046HCID 19875046, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 14404121HCID 14404121, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of [3-(1-hydroxyethyl)phenylsulphonyl]nitromethane (1.10 g, 4.5 mmol) in dichloromethane (10 ml) was added to a vigorously stirred suspension of pyridinium chlorochromate (1.45 g, 6.7 mmol) in dichloromethane (10 ml). The mixture was stirred for 2 hours. Ethyl acetate (100 ml) was added and the solvent was decanted. The black residue was washed twice with ethyl acetate. The extracts and the decanted solution were combined and filtered through magnesium silicate [`Florisil` (trade mark)]. The solvent was evaporated. The residual yellow solid was recrystallised from toluene to give (3-acetylphenylsulphonyl)nitromethane, as a solid, (0.67 g), m.p. 99°-100° C., microanalysis, found: c, 44.7; H, 3.8; N, 5.7%; C9H9NO5S requires: C, 44.4; H, 3.7; N, 5.8%.

Workup

  1. customthe solvent was decanted
  2. washThe black residue was washed twice with ethyl acetate
  3. filtrationfiltered through magnesium silicate [`Florisil` (trade mark)]
  4. customThe solvent was evaporated
  5. customThe residual yellow solid was recrystallised from toluene

Sources & evidence

ORD record
ord-9f36e81ae7204468b7f93aa60f817e7c
Source dataset
uspto-grants-1992_10
Patent number
US05153227

Reaction notes

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