Benzene, [1-[(trimethylsilyl)oxy]ethenyl]- → Acetophenone

HRID 1026839Notes

Reaction equation

HRID 1026839 reaction equation
[C:1]1([C:7]([O:9][Si](C)(C)C)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(F)(F)C([O-])=O.[Na+]>COCCOCCOC>[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])[CH3:8]

Participants

4

Reactant 2

HCID 117406Benzene, [1-[(trimethylsilyl)oxy]ethenyl]-2×HCID 2734985Sodium chlorodifluoroacetate

Product 1

HCID 7410Acetophenone

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

Specifically, (1-phenylvinyloxy)-trimethylsilane (Compound 1g; 61.3 mg, 0.32 mmol) and diglyme (1.0 mL) were put into a two-neck evacuation flask under nitrogen atmosphere, and a diglyme (3.0 mL) solution of sodium chlorodifluoroacetate (292 mg, 1.9 mmol) was added dropwise to the mixture at 180° C. for 55 minutes, and then the mixture was stirred for 5 minutes. The reaction mixture was washed with water, and then dried with sodium sulfate. The solvent was distilled away under reduced pressure, and then the residue was subjected to GC/MS measurement. As a result, Compound 2g, Compound 3, Compound 4 and acetophenone (Compound 5) were obtained with yields of 23%, 5%, 20% and 6%, respectively.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried with sodium sulfate
  3. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-a970797af72b4686b6a886f7f8bb725b
Source dataset
uspto-grants-2014_05
Patent number
US08729320B2

Reaction notes

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