3-Bromo-1-propanol → 3-(4'-Cyano-4-biphenylyl)-1-propanol

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Reaction Steps

4'-Cyano-4-hydroxybiphenyl (6 g, 0.02 mol) and 3-bromo-1-propanol (5.6 g, 0.04 mol) were dissolved in ethanol (300 ml), followed by gradually dropwise adding an aqueous solution of sodium hydroxide (10 g) in water (20 ml) over 30 minutes, continuing, as it was, stirring for 40 hours, thereafter distilling off ethanol (about 200 ml) under reduced pressure, then adding water (500 ml), extracting the resulting deposited crystals three times with toluene (100 ml), removing insoluble matter by filtration, washing the toluene layer twice with a 2N aqueous solution of NaOH, further 3 times with water, drying over anhydrous sodium sulfate, completely distilling off toluene and recrystallizing the residual crystals from methanol to prepare 3-(4'-cyano-4-biphenylyl)-1-propanol. Yield: 2 g (28%). This product exhibited liquid crystal phases and its C-N point was 109.0°~110.7° C. and its N-I point was 113.6° C.

Provenance & Evidence