Bogert-Cook synthesis

Follow the instructions for Problem 30.26 for the foHowtng synthesis of phenanthrene (the Bogert-Cook synthesis). 

Bogert-Cook synthesis. Condensation of (1-phenylethylmagnesium bromide with cyclohexanones, followed by cyclodehydration of the tertiary alcohol with concentrated sulfuric acid, with formation of octahydrophenanthrene derivatives and a small amount of spiran. 

Other references related to the Bogert-Cook synthesis are cited in the literature. ... 

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

Problem 30.30 Outline a possible synthesis of chrysene by the Bogert-Cook method (Problem 30.27, p. 944), starting from naphthalene and using any aliphatic or inorganic reagents. Hint See Problem 30.7(g), p. 977.)... 

ProUem 30.31 Outline an alternative synthesis of chrysene by the Bogert-Cook methodi starting from benzene and using any aliphatic or inorganic reagents. 

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. 

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 ... 

Much like the work conducted by the Bogert and Cook groups, the Bardhan-Sengupta synthesis of phenanthrenes helped lead to the determination of the carbon framework for steroids and was used to prepare terpene-type natural products. 

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