Bogert-Cook reaction

An alkene unit can also be used to generate a cation and cyclize to form a polycyclic aromatic compound. When 229 reacted with acetaldehyde, 230 was produced and this was cyclized by treatment with sulfuric acid to give hydronapthalene (231). This modification does not incorporate the additional ring of the cyclic ketones used in the Bogert-Cook reaction it is sometimes called the Bogert synthesis. 

Bogert-Cook Reaction Timothy T. Curran 4.3.1 Description... 

The mechanism of the Bogert-Cook reaction has been shown to be substrate dependent and different transition states have been used to explain different products observed. However, in general, starting with an alcoholic substrate 19a,b, protonation of the hydroxyl group and loss of water to generate the carbocation 20a,b (which could either result in alkene formation, cyclization. 

It is a solid substance having a melting point 126-127°C and a molecular formula CigHjg. Based on the results of oxidation reactions. X-rays crystal analysis coupled with absorption spectrum measurements it was revealed that the hydrocarbon in question could be 3 -methyl-l 2-cyclopentanophenanthrene. The next essential step was to establish the structure of this compound by synthesis, e.g., that of Harper a/ (1934) who used the Bogert-Cook method commencing from ... 

Bodroux-Chichibabin Aldehyde Synthesis Bogert-Cook Synthesis Bohn-Schmidt Reaction... 

---