Ethyl Acetate → HCID 66756947, compound

HRID 1642618Notes

Reaction equation

HRID 1642618 reaction equation
[Cl:1][CH2:2][C:3]1[C:4]([CH2:9]Cl)=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH3:11][S:12]([O-:14])=[O:13].[Na+].CCOC(C)=O>CN(C=O)C>[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][S:12]([CH3:11])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 119191,2-Bis(chloromethyl)benzeneHCID 2733271Sodium methanesulfinate

Product 1

HCID 66756947HCID 66756947, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of α,α′-dichloro-o-xylene (3.5 g, 18 mmol) in DMF (20 mL) is added sodium methanesulfinate (0.612 g, 6.0 mmol) and the mixture is stirred at 65° C. for 4 h. Ice/water and EtOAc are added, the phases are separated and the organic phase is washed with water and brine, dried over Na2SO4/MgSO4, filtered and concentrated. The resulting residue is chromatographed on silica gel, eluting with a gradient of hexane/EtOAc to afford 1-chloromethyl-2-methanesulfonylmethylbenzene as a white solid: MS (M+NH4)+=236.

Workup

  1. customthe phases are separated
  2. washthe organic phase is washed with water and brine
  3. dry with materialdried over Na2SO4/MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue is chromatographed on silica gel
  7. washeluting with a gradient of hexane/EtOAc

Sources & evidence

ORD record
ord-8410c3a60601456582d5273f2994913f
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

Loading…