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 300cc and a Friedel Craft's reaction is effected in 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 a mixed solution of 100cc pyridine and 50cc. of benzene. After this 0.012 mole of 4-octyloxy-benzoil chloride is added to the solution, this mixed solution is heated and stirred for 24 hours. Extraction is achieved by adding water (200cc) and benzene (100cc) to the solution. The resultant benzene layer is washed with a mixture of 1 mole of sodium hydroxide solution (50cc) and 1 mole of HCl liquid (100cc). The resultant compound in benzene layer is crystallized from ethyl alcohol (50cc). The result of the above method steps, 4-octyl-4'-(4"-octyloxy benzoil)-3'-chlorobiphenyl (Compound 1 in the above table), is extracted at the yield rate of 85%.

Provenance & Evidence