2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 9-Chlorodibenzothiophene-3-acetic acid ethyl ester

HRID 1856523Notes

Reaction equation

HRID 1856523 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[CH2:15]([O:17][C:18](=[O:34])[CH2:19][CH:20]1[CH2:33][C:24]2[S:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=3[C:23]=2[CH2:22][CH2:21]1)[CH3:16]>O1CCOCC1>[CH2:15]([O:17][C:18](=[O:34])[CH2:19][C:20]1[CH:21]=[CH:22][C:23]2[C:27]3[C:28]([Cl:32])=[CH:29][CH:30]=[CH:31][C:26]=3[S:25][C:24]=2[CH:33]=1)[CH3:16]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 130651369-Chloro-1,2,3,4-tetrahydrodibenzothiophene-3-acetic acid ethyl ester

Product 1

HCID 130651209-Chlorodibenzothiophene-3-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a 1-l. three-necked flask provided with a condenser, stirrer and dropping funnel was added 11 g. of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and 500 ml. of dioxane. To the solution heated to reflux, was added at a rapid rate a solution of 6 g. of 9-chloro-1,2,3,4-tetrahydrodibenzothiophene-3-acetic acid ethyl ester in 100 ml. of dioxane. The solution was refluxed and stirred for 24 hours, cooled to room temperature and then filtered to remove the hydroquinone. The solvent was removed in vacuo on the steam bath, and the residue was dissolved in 200 ml. of methylene chloride. This solution was passed through a column containing about 150 g. of alumina (Woelm, grade 1). The solvent was removed on the steam bath and the residue was crystallized from alcohol. The yield of 9-chlorodibenzothiophene-3-acetic acid ethyl ester was 1.1 g., m.p. 82°-84°.

Workup

  1. customthree-necked flask provided with a condenser, stirrer
  2. additionwas added 11 g
  3. temperatureTo the solution heated
  4. temperatureto reflux
  5. additionwas added at a rapid rate a solution of 6 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 200 ml
  11. additioncontaining about 150 g
  12. customThe solvent was removed on the steam bath
  13. customthe residue was crystallized from alcohol

Sources & evidence

ORD record
ord-60764010519e4c75ba0f3e3a0bbfd4bd
Source dataset
uspto-grants-1980_08
Patent number
US04219657

Reaction notes

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