Chloroacetone → 7-Chloro-3-methyl-1-benzothiophene

HRID 1380077Notes

Reaction equation

HRID 1380077 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Cl[CH2:10][C:11](=O)[CH3:12]>[OH-].[Na+]>[Cl:1][C:2]1[C:3]2[S:8][CH:10]=[C:11]([CH3:12])[C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 80599o-Chlorothiophenol

Product 1

HCID 202421187-Chloro-3-methyl-1-benzothiophene

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 11.8 g. 2-chlorothiophenol (Aldrich, 15566-7) dissolved in aqueous sodium hydroxide (4.0 g./50 ml water) is added chloracetone (9.3 g.). After heating for 1 hour the reaction is cooled and extracted with methylene chloride. The extract is dried (MgSO4) and concentrated to an oil. The oil is added to polyphosphoric acid (100 g.) and slowly heated to 120° C. The mixture is added to ice and extracted with ethyl ether. The ether extract is washed with water (twice); dried (MgSO4) and concentrated to an oil. The oil is purified by distillation.

Workup

  1. temperatureAfter heating for 1 hour the reaction
  2. temperatureis cooled
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract is dried (MgSO4)
  5. concentrationconcentrated to an oil
  6. additionThe oil is added to polyphosphoric acid (100 g.)
  7. additionThe mixture is added to ice
  8. extractionextracted with ethyl ether
  9. extractionThe ether extract
  10. washis washed with water (twice)
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated to an oil
  13. distillationThe oil is purified by distillation

Sources & evidence

ORD record
ord-c34a80122c4e4924a7c39baded00cb9e
Source dataset
uspto-grants-1986_04
Patent number
US04579865

Reaction notes

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