Chardonnens, Louis; Wurmli, Albert published an article in 1946, the title of the article was Derivatives of fluorenone. II. 3,6-Dimethylfluorenone.Application In Synthesis of 5,5′-Dimethyl-[1,1′-biphenyl]-2,2′-dicarboxylic acid And the article contains the following content:
cf. C.A. 40, 1479.2. Diazotization of 4,2-Me(H2N)C6H3CO2H (I) and treatment of the solution with NH3-Cu2O gives 84% 5,5′-dimethyl-2,2′-dicarboxybiphenyl, m. 269° (all m.ps. corrected). When this is mixed with CaO and heated 2 hrs. at 350° it gives 23% 3,6-dimethylfluorenone (II), m. 118° (oxime m. 189-91°), but the product is always contaminated with a red oil which can be separated only by chromatography. It is therefore better to treat I with NaOH and MeC6H4SO2Cl to get 77% 4-methyl-2-tosylaminobenzoic acid, m. 208-9°. With PCl5 this gives the acid chloride which reacts with MePh and AlCl3. The product is saponified to give 65% 4,4′-dimethyl-2-aminobenzophenone (III), m. 119°. 4,4′-Dimethyldiphenyl sulfone is a by-product. Diazotization of III in H2SO4 gives 70% II and a little 4,4′-dimethyl-2-hydroxybenzophenone, m. 73-4°. When II is heated 6 hrs. at 175° in a sealed tube with N2H4.H2O and Na in EtOH, it gives 85% 3,6-dimethylfluorene, m. 130-1°. Direct nitration of II with H2SO4 and KNO3 gives only 3,6-dimethyl-2,7-dinitrofluorenone (IV), m. 281° (decomposition). The mononitro compound cannot be prepared in this way. 4-Methyl-5-nitro-2-chlorobenzoic acid is converted to the acid chloride which, with MePh and AlCl3, gives 69% 4,4′-dimethyl-5-nitro-2-chlorobenzophenone, m. 108.5°. This heated 8 hrs. in a sealed tube at 160-70° with alc. NH3 gives 82% 4,4′-dimethyl-2-amino-5-nitrobenzophenone, m. 162.5°. This is diazotized in H2SO4 to give 59% 3,6-dimethyl-2-nitrofluorenone (V), m. 222-4°, and some 4,4′-dimethyl-5-nitro-2-hydroxybenzophenone, m. 144°. Nitration of V gives IV. The experimental process involved the reaction of 5,5′-Dimethyl-[1,1′-biphenyl]-2,2′-dicarboxylic acid(cas: 93012-36-3).Application In Synthesis of 5,5′-Dimethyl-[1,1′-biphenyl]-2,2′-dicarboxylic acid
5,5′-Dimethyl-[1,1′-biphenyl]-2,2′-dicarboxylic acid(cas:93012-36-3) belongs to chlorides. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst. Application In Synthesis of 5,5′-Dimethyl-[1,1′-biphenyl]-2,2′-dicarboxylic acid
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics