2-Chloro-4-Phenylphenol → 4-Octyl-4'-methoxy-3'-chlorobiphenyl

Participants

Reaction Steps

4-phenyl-2-chlorophenol is methylated by means of well-known method steps and 4-phenyl-2-chloroanisole (hereinafter referred to as Material I) is extracted. 1/3 mole of Material I is dissolved into carbon disulfide 300 cc and a Friedel-Craft's reaction is effected a MILO flask in which 1/3 mole of octanol chloride and 60 grams of anhydrous ammonium chloride are placed. As a result, 4-octanoyl-4'-methoxy-3'-chlorobiphenyl (hereinafter referred to as Compound 4) is extracted with a yield of 75%. As the result of reduction of said Compound 4, by the well-known Wolff-Kischner's reaction, 4-octyl-4'-methoxy-3'-chlorobiphenyl (hereinafter referred to as Compound 5) is extracted with a yield of 70 weight percent. 0.01 mole of 4-octyl-4'-hydroxy-3-chlorobiphenyl (hereinafter referred to as Material II) which is extracted from said Compound 5 by means of demethylation with HBr water, is dissolved into mixed solution of 100 cc of pyridine and 50 cc of benzene. After this 0.012 mole of 4-octyloxy benzoic chloride is added to the solution, this mixed solution is heated and stirred for 24 hours. An extraction process is achieved by adding water (200 cc) and benzene (100 cc) into the solution. The resultant benzene layer is washed with a mixture of 1 mole of sodium hydroxide solution (50 cc) and 1 mole of HCl liquid (100 cc). After the resultant compound in benzene layer is left through the washing, it is crystallized from ethyl alcohol (50 cc). The result of the above method steps, 4-octyl-4'-(4"-octyloxy benzoil)-3'-chrobiphenyl (Compound 1 in the above table) is extracted at the yield rate of 85%.

Provenance & Evidence