Hydrochloric Acid → HCID 23330686, compound

HRID 224910Notes

Reaction equation

HRID 224910 reaction equation
C[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=S.[Cl-].[Al+3].[Cl-].[Cl-].Cl.[C:18](=S)=[S:19]>>[CH3:18][S:19][C:9]1[CH:10]=[CH:11][CH:12]=[C:2]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:8]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 6451240Aluminum(III) ChlorideHCID 178424225HCID 178424225, compound

Product 1

HCID 23330686HCID 23330686, compound

Procedure

To a solution of 50 g of o-methylthiocinnamic acid in 500 ml of carbon disulfide was gradually added with stirring 34 g of aluminum chloride, and the resulting mixture was then boiled with stirring for 3 hours. The reaction liquid after reaction was poured into a cooled 1 N aqueous hydrochloric acid solution and extracted with ethyl acetate. The ethyl acetate solution was washed with an aqueous potassium carbonate solution, followed by water-washing and then drying over anhydrous sodium sulfate, to remove the solvent therefrom. The residue was purified by column chromatography to obtain 18 g of the title compound.

Workup

  1. customThe reaction liquid
  2. customafter reaction
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate solution was washed with an aqueous potassium carbonate solution
  5. washwashing
  6. dry with materialdrying over anhydrous sodium sulfate
  7. customto remove the solvent
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-95ec45265c0340d4a6e5716163b0158b
Source dataset
uspto-grants-1980_11
Patent number
US04234678

Reaction notes

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