HCID 21281102, compound → HCID 53946059, compound

HRID 414581Notes

Reaction equation

HRID 414581 reaction equation
[C:1]1([CH:7]([CH3:21])[CH:8]([C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>Cl>[C:1]1([C:7]([CH3:21])=[CH:8][C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 21281102HCID 21281102, compound

Product 1

HCID 53946059HCID 53946059, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred mixture of 8.0 grams (0.027 mole) of 2-phenyl-1-(5-phenylthien-2-yl)-1-propanol in 100 mL of concentrated hydrochloric acid was heated at reflux for 1.5 hours. The mixture was cooled and extracted with chloroform. The extract was washed with an aqueous solution saturated with sodium chloride and dried over anhydrous magnesium sulfate. The mixture was filtered, and the filtrate was evaporated under reduced pressure yielding a solid residue. Half of this residue was purified by column chromatography on silica gel, eluting with toluene:n-hexane (5:95). The remainder of the residue was purified by recrystallization from toluene and ethanol to yield a total of 4.0 grams of 2-phenyl-1-(5-phenylthien-2-yl)-1-propene as a solid, m.p. 115°-25° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with chloroform
  5. washThe extract was washed with an aqueous solution saturated with sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe mixture was filtered
  8. customthe filtrate was evaporated under reduced pressure
  9. customyielding a solid residue
  10. customHalf of this residue was purified by column chromatography on silica gel
  11. washeluting with toluene:n-hexane (5:95)
  12. customThe remainder of the residue was purified by recrystallization from toluene and ethanol

Sources & evidence

ORD record
ord-8d8d233c6f74459383f936894ca87cab
Source dataset
uspto-grants-1988_12
Patent number
US04792567

Reaction notes

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