Methanol → (1,1'-Biphenyl)-2,3'-diol

Participants

Reaction Steps

Bis-(p-methoxyphenyl)-cyclohexylidene methane 28 (FIG. 3) was prepared from methyl cyclohexane carboxylate 26 and p-methoxyphenyl magnesium bromide (Miquel et al., 1963). Dehydration of 27 was accomplished with a mixture of H2SO4 and acetic acid. While 29 was demethylated with iodotrimethylsilane in pyridine, 30 was difficult to isolate, and the demethylation was repeated using n-BuSH/AlCl3. However, the best method found for demethylation involved the use of EtSH/AlCl3 in CH2Cl2. EtSH has a lower boiling point than n-BuSH and offers the advantage of being easier to remove from the reaction mixture. Diphenol 30 underwent a gradual color change, but was obtained pure from the acid hydrolysis of the di-acetate 31.

Provenance & Evidence