O-Xylene → HCID 131717672, compound

HRID 1681236Notes

Reaction equation

HRID 1681236 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=1[CH3:14].C([Li])CCC.Cl[CH:21]([SiH3:23])Cl>CCCCCC.O>[CH3:21][SiH:23]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1

Participants

7

Reactant 4

HCID 7237O-Xylene2×HCID 23665647Potassium tert-butoxideHCID 57353436(Dichloromethyl)silaneHCID 178418339Butyllithium

Product 1

HCID 131717672HCID 131717672, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

In a 1 L rb flask equipped with a Teflon covered magnetic stirring bar and a reflux condenser was placed potassium tert-butoxide (36 g; 0.32 mol), o-xylene (17 mL; 0.15 mol) and 700 mL of hexanes. n-Butyllithium (128 mL; 2.5M) in hexane was added to the above mixture via a syringe. The red color of the o-xylene dianion appeared. The resulting mixture was heated to reflux for 1 h. The reaction mixture was cooled to room temp. The suspension of the dianion was transferred via a cannula to a sintered glass filter. The solvent was removed by suction filtration. The precipitated dianion was rinsed with fresh hexane. It was then resuspended in 500 mL of hexane and the suspension returned via a cannula to the original apparatus. Freshly distilled dichloromethylsilane (17 mL; 0.16 mol) was added. The mixture was stirred overnight a room temperature. 50 mL water was added. The organic layer was washed three times with water, dried over anhydrous calcium chloride, filtered and the solvents removed by evaporation under reduced pressure. The residue was purified by fractional distillation through a 15 cm vacuum jacketed Vigreux column. A central fraction, b.p. 43°-44° C./0.7 mmHg, was obtained. Yield: 5.5 g(25%).

Workup

  1. customIn a 1 L rb flask equipped with a Teflon covered magnetic stirring bar and a reflux condenser
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux for 1 h
  4. additionThe suspension of the dianion
  5. filtrationfilter
  6. customThe solvent was removed by suction filtration
  7. washThe precipitated dianion was rinsed with fresh hexane
  8. washThe organic layer was washed three times with water
  9. dry with materialdried over anhydrous calcium chloride
  10. filtrationfiltered
  11. customthe solvents removed by evaporation under reduced pressure
  12. distillationThe residue was purified by fractional distillation through a 15 cm vacuum
  13. customA central fraction, b.p. 43°-44° C./0.7 mmHg, was obtained

Sources & evidence

ORD record
ord-3e654dca7eef4a1087b8a10392113630
Source dataset
uspto-grants-1992_12
Patent number
US05169916

Reaction notes

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