4:4-dihydroxydiphenylquinolylmethanes and 4:4-dihydroxydiphenyl-iso-quinolylmethanesand the preparation thereof

摘要

The invention comprises compounds of the formula FORM:0735683/IV (b)/1 where Q is a quinoline or isoquinoline residue (which may be alkyl-substituted), R is hydro gen, alkyl, aryl, aralkyl, alkoxy or acyloxy, X is hydrogen, alkyl or acyl, R1 is hydrogen or alkyl and n is 1-4. Preferably the alkyl and acyl groups have 1-6 carbon atoms, the aryl 6 or 10 and the aralkyl 7-16. The compounds are made by condensing two mols. of the appropriate phenol (or ester or ether thereof) with a quinoline or isoquinoline aldehyde or ketone in the presence of a water-binding substance such as sulphuric acid, phosphoric acid, hydrochloric acid, zinc chloride, stannic chloride, a phosphorus halide, phosphorus pentoxide, boron trifluoride or aluminium chloride. The reaction may be carried out in a solvent such as benzene or toluene. It is usually desirable to apply cooling and agitation, although sometimes warming is necessary. The free hydroxy groups in the product (X = H) may be subsequently etherified or esterified. In the examples the following are made by direct condensation: bis - (4 - hydroxyphenyl) - (quinolyl - 2) - methane, bis - (4 - hydroxy - 3 - methyl) - (quinolyl - 2) - methane, bis - (4 - hydroxyphenyl)-(6 - methylquinolyl - 2) - methane, bis - (4-hydroxyphenyl) - (isoquinolyl - 3) - methane, bis - (4 - hydroxyphenyl) - (isoquinolyl - 1) - methane, bis - (4 - hydroxy - 3 - methoxyphenyl)-(quinolyl - 2) - methane, bis - (4 - methoxyphenyl) - (quinolyl - 4) - methane, bis-(4-hydroxy - 3 - isopropyl - 6 - methylphenyl)-(quinolyl - 4) - methane, bis - (4 - hydroxy - 3-phenylphenyl) - (quinolyl - 4) - methane, bis-(4 - hydroxy - 3 - benzylphenyl) - (quinolyl - 4)-methane, 1 : 1 - bis - (4 - hydroxyphenyl) - 1-(quinolyl - 2) - ethane and 1 : 1 - bis - (4-hydroxyphenyl) - 1 - (isoquinolyl - 1) - ethane. Bis - (4 - acetoxyphenyl) - (quinolyl - 2) - methane is prepared by acetylation of the dihydroxy compound.