《Chiral Organomagnesiates as Dual Reagents for Bromine-Magnesium Exchange of 2-Bromopyridine and Access to Chiral α-Substituted 2-Pyridylcarbinols》 was published in European Journal of Organic Chemistry in 2012. These research results belong to Catel, Delphine; Chevallier, Floris; Mongin, Florence; Gros, Philippe C.. Synthetic Route of C24H34O2 The article mentions the following:
Magnesiates generated from butyllithium, butylmagnesium chloride, and racemic or nonracemic diols such as rac-BINOL or (R,R)-TADDOL chemoselectively metalated 2-bromopyridine; reaction of the intermediate metalated pyridine with aldehydes yielded α-substituted 2-pyridinemethanols chemoselectively in 58-85% yields. Using a magnesiate derived from (R,R)-TADDOL, dibutylmagnesium, and butyllithium, 2-bromopyridine underwent enantioselective metal-bromine exchange and addition to 4-methoxybenzaldehyde to give α-(4-methoxyphenyl)-2-pyridinemethanol in 28% yield and in 76% ee. In addition to this study using (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol, there are many other studies that have used (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Synthetic Route of C24H34O2) was used in this study.
(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols.Synthetic Route of C24H34O2 The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts