The Preparation and Germicidal Properties of Some Alkyl Derivatives of Hydroxy Diphenyls**Scientific Section, A. PH. A, Madison meeting, 1933.

Relationships between the Structure and the Bactericidal Properties of Phenols.

“…2,5-Dihydroxybiphenyl requires a dilution of 1:500 to kill either B. typhosus or Staph, aureus in 5 min. (56), while for the 3,4-isomer the dilutions were 1:2000 and 1:1200, respectively.…”

“…Although there are many claims in the patent literature and some general statements elsewhere to the effect that hydroxybiphenyls are excellent bactericidal agents, the quantitative information available is small. Harris and Christiansen (56) have shown that 2-hydroxybiphenyl kills B. typhosus in a dilution of 1:2000 in 5 min., while against Staph, aureus the dilution necessary is 1:800. Woodruff gives the phenol coefficient here as 12.5 <23.…”

“…A recent (104) determination of the behavior of 3-hydroxybiphenyl toward Staph, aureus gave a phenol coefficient of 33, indicating that phenyl is somewhat less effective than n-butyl in increasing the germicidal action of phenol. The activity toward B. typhosus is only about one-fifth as great (56). Against Staph, aureus, p-phenylphenol is even less effective than the ortho-isomer (162).…”

The Fries Reaction.

“…The shift of an acyl group to a hydroxyl-free ring, the formation of heteronuclear hydroxy ketones, has also been encountered in the biphenyl series. Aliphatic esters of 2-hydroxybiphenyl are reported to furnish mixtures of 3-and 5-acyl-2-hydroxybiphenyls (3), the yield of the 3-acyl derivatives increasing with the size of the acyl group (31). The structures assigned the hydroxy ketones are reasonable but have never been proved.…”

“…COR Esters of the 3,4-and 2,5-dihydroxybiphenyls yield tars only (31). In the phenanthrene series, the Fries reaction leads to hydroxy ketones whose structures in certain cases have not been unequivocally established and the reaction offers no advantages over the Friedel-Crafts reaction (48).…”