</title> </titles> <publication_date media_type='online'> <year>2015</year> </publication_date> <doi_data> <doi></doi> <resource></resource> </doi_data> </journal_article> <!-- ============== --> <journal_article publication_type='full_text'> <titles> <title>2-THIOPHENEALDEHYDE

The flask is fitted for steam distillation, and steam is passed in until all the aldehyde has distilled

Kenneth Wiberg

2015

Scholarcy highlights

  • The hexamethylenetetrammonium salt is placed in a 2-l
  • The flask is fitted for steam distillation, and steam is passed in until all the aldehyde has distilled
  • The distillate is cooled, 10 ml. of 6 Nacetic acid is added, and the aldehyde is extracted with two 100-ml. portions of ether
  • The ether solution is dried over anhydrous calcium chloride, and the ether is evaporated on a steam bath until the volume of the solution has decreased to about 50 ml
  • The crude product is distilled through a short column under reduced pressure; after a fore-run of acetic acid the product is collected at 63–66°/6 mm. or 115–118°/65 mm
  • 2-Thiophenealdehyde has been prepared by the decarboxylation of 2-thienylglyoxalic acid, by the action of 2-thienylmagnesium iodide on ethyl orthoformate followed by hydrolysis of the acetal, in small yields by the Rosenmund reduction of 2-thiophenecarboxylic acid chloride, in small yields by the action of hydrogen cyanide, hydrogen chloride, and aluminum chloride on thiophene, using benzene as a solvent, by a series of reactions from 1-chloro-2,3-diketocyclopentane, by the hydrolysis of 2-thenylmethylhexamethylenetetrammonium chloride in neutral solution, by the action of N-methylformanilide on thiophene in the presence of phosphorus oxychloride, by the acid hydrolysis of N-(2-thenyl)-2'-thenaldimine, and by the oxidation of N,N-di-(2-thenyl)hydroxylamine with alkaline potassium permanganate

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