Preparation of 2,2'-dihydroxytriphenylmethanes using metal phenolates with aromatic aldehydes.
The reactions of oxophilic metal phenolates having electron-donating substituents (1a-c) with aromatic aldehydes (2, 3) were selectively condensed at the ortho-position of the starting phenol to afford 2,2'-dihydroxytriphenylmethanes (8-11). This method was also applicable to the preparation of bisphenols (12-17) starting with naphthaldehydes (4, 5) and pyridinecarboxaldehydes (6, 7), but in low yields. In the case of these aldehydes (4-7), satisfactory yields could be obtained by sonication.
Mibu
N
N
Faculty of Pharmaceutical Sciences, Fukuoka University, Japan.
Sumoto
K
K
D000447:Aldehydes / Q000737:chemistry*; D008274:Magnesium; D009682:Magnetic Resonance Spectroscopy; D010636:Phenols / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D014320:Triphenylmethyl Compounds / Q000138:chemical synthesis*
D000447:Aldehydes; D010636:Phenols; D014320:Triphenylmethyl Compounds; D008274:Magnesium