4,4'-Dihydroxybiphenyl → HCID 70254186, compound

Participants

Reaction Conditions

Reaction Steps

Following the procedure of Example 6, 18.6 g (0.1 mol) of biphenyl-4,4'-diol (Merck, 64271 Darmstadt, Delaware) were reacted with 42.6 g (0.2 mol) of 6-bromohexanoyl chloride in toluene using triethylamine as acid scavenger. This gave 42 g (77.8%) of 4,4'-biphenyl bis(6-bromohexanoate) of m.p. 96° C. 35 g (0.065 mol) of this compound and 25 g (0.2 mol) of potassium methacrylate were suspended in 30 ml of dimethylformamide, 0.04 g of BHT was added, and the mixture was heated at 95° C. with stirring for 6.5 h. It was then cooled and taken up in water and methyl tert-butyl ether, and the two phases which formed were separated. Washing, drying and concentration of the organic phase gave a crude product which following recrystallization from methanol has a melting range of 50-59° C. and on cooling to 56° C. shows a supercoolable smectic phase.

Provenance & Evidence