2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 13065108, compound

HRID 1856527Notes

Reaction equation

HRID 1856527 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[CH2:15]([O:17][C:18]([CH:20]1[CH2:33][C:24]2[S:25][C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:27]=3[C:23]=2[CH2:22][CH2:21]1)=[O:19])[CH3:16]>O1CCOCC1>[CH2:15]([O:17][C:18]([C:20]1[CH:21]=[CH:22][C:23]2[C:27]3[CH:28]=[C:29]([CH3:32])[CH:30]=[CH:31][C:26]=3[S:25][C:24]=2[CH:33]=1)=[O:19])[CH3:16]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 13065137HCID 13065137, compound

Product 1

HCID 13065108HCID 13065108, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a 500 ml. three-necked flask provided with a condenser, stirrer and dropping funnel was added 10 g. of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and 200 ml. of dioxane. To the solution, heated to reflux, was added at a rapid rate a solution of 5.5 g. of 8-methyl-1,2,3,4-tetrahydrodibenzothiophene-3-carboxylic acid ethyl ester in 50 ml. of dioxane. The solution was refluxed and stirred for 20 hours, cooled to room temperature and filtered to remove the hydroquinone. The solvent was removed in vacuo on the steam bath, and the residue was dissolved in 100 ml. of methylene chloride. The solution was passed through a column containing about 75 g. of alumina (Woelm, grade I). The solvent was removed, and the residue was crystallized from methanol. The yield of 8-methyldibenzothiophene-3-carboxylic acid ethyl ester was 4.2 g., m.p. 83°-87°.

Workup

  1. customthree-necked flask provided with a condenser, stirrer
  2. additionwas added 10 g
  3. temperatureTo the solution, heated
  4. temperatureto reflux
  5. additionwas added at a rapid rate a solution of 5.5 g
  6. temperatureThe solution was refluxed
  7. filtrationfiltered
  8. customto remove the hydroquinone
  9. customThe solvent was removed in vacuo on the steam bath
  10. dissolutionthe residue was dissolved in 100 ml
  11. additioncontaining about 75 g
  12. customThe solvent was removed
  13. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-7c0c6b0100184f3bbc6bf9852ae76cae
Source dataset
uspto-grants-1980_08
Patent number
US04219657

Reaction notes

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