Chlorobenzene → HCID 9921792, compound

HRID 866768Notes

Reaction equation

HRID 866768 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:11]Cl)=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:17]3[C:16](=[CH:15][C:14]([Cl:13])=[CH:19][CH:18]=3)[C:7](=[O:8])[C:6]=2[CH:10]=1

Participants

6

Reactant 4

HCID 7964ChlorobenzeneHCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 148124695-Chloro-2-(chlorosulfanyl)benzoyl chloride

Product 1

HCID 9921792HCID 9921792, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

One half of the solution of 5-chloro-2-chlorosulfenylbenzoyl chloride (135 ml of 0.05 mole of Example 4) was charged into 200 ml three neck flask equipped similarly as the reaction flask in Example 4. About 11.2 g of chlorobenzene was added and at the temperature of this mixture maintained in the range of 20°-30° C while 6.75 g of powdered aluminum chloride (0.05 mole) was charged in small portions in approximately 30 minutes. After the charging the batch was stirred for an additional 1 hour, while the temperature was maintained in the range of 25°-30° C. The crystalline aluminum chloride complex, which separated from the solution, was filtered and the cake was washed with hexane. The cake was then treated with 1.3 mole NaOH dissolved in 300 ml of water. The isolated product, 10 g of light yellow crystalline powder (m.p. 230C) was crude 2,7-dichloro-thioxanthen-9-one (70% yield).

Workup

  1. customequipped similarly as the reaction flask in Example 4
  2. additionwas charged in small portions in approximately 30 minutes
  3. temperaturewas maintained in the range of 25°-30° C
  4. customThe crystalline aluminum chloride complex, which separated from the solution
  5. filtrationwas filtered
  6. washthe cake was washed with hexane

Sources & evidence

ORD record
ord-dac1a2c04b974de99255ead10eab7ea1
Source dataset
uspto-grants-1978_07
Patent number
US04101558

Reaction notes

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