Acetone → HCID 22151702, compound

HRID 703256Notes

Reaction equation

HRID 703256 reaction equation
[CH3:1][Si:2]([CH3:16])([CH3:15])[C:3]1[CH:8]=[CH:7][C:6]([CH:9](Br)Br)=[C:5]([CH:12](Br)Br)[CH:4]=1.[I-].[Na+].[CH3:19][C:20]([CH3:22])=[O:21]>C(#N)C>[CH3:1][Si:2]([CH3:16])([CH3:15])[C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[CH:9]=[C:22]1[C:19]([C:20](=[O:21])[C:22]3[CH:8]=[CH:3][CH:4]=[CH:5][C:19]=3[C:20]1=[O:21])=[CH:12]2

Participants

5

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 13782825HCID 13782825, compound

Product 1

HCID 22151702HCID 22151702, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.1 mol of 4-trimethylsilyl-1,2-bisdibromomethylbenzene, 0.12-0.2 mol of substituted naphthoquinone, 0.6 mol of sodium iodide and 1000 ml of acetone or acetonitrile is boiled under reflux for 5 hours with stirring and under an N2 atomosphere. After cooling, the precipitate which has been deposited is filtered off and digested with water. The filtrate obtained in this way is evaporated to dryness and the residue is dissolved in CH2Cl2, washed with NaHSO3 and dried. The residue is then subjected to steam distillation and the non-volatile fractions are extracted with ether, dried and then sublimed. 8-Trimethylsilylnaphthacene-5,12-dione of melting point 168°-170° C. is obtained in a 79% yield. 2,3-Trifluoromethyl-8-methoxynaphthacene-5,12-dione is obtained in a 33% yield in an analogous manner by direct sublimation of the filtrate, melting point>280° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitate which has been deposited is filtered off
  4. customThe filtrate obtained in this way
  5. customis evaporated to dryness
  6. dissolutionthe residue is dissolved in CH2Cl2
  7. washwashed with NaHSO3
  8. customdried
  9. distillationThe residue is then subjected to steam distillation
  10. extractionthe non-volatile fractions are extracted with ether
  11. customdried

Sources & evidence

ORD record
ord-fe787efde18b4faebe46d5189affe56a
Source dataset
uspto-grants-1991_01
Patent number
US04981962

Reaction notes

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