Formula: C9H12O2On March 28, 1979, Kende, Andrew S.; Curran, Dennis P. published an article in Journal of the American Chemical Society. The article was 《Regiochemical control in dihydrophenanthrene synthesis. A photochemical total synthesis of juncusol》. The article mentions the following:
Three approaches are described toward the total synthesis of juncusol (I), a cytotoxic constituent of the needlerush Juncus roemerianus. Wittig condensation of the phosphonium salt derived from 2-methyl-3-methoxybenzyl bromide with 3-methoxy-4-methyl-5-cyanobenzaldehyde gave a mixture of cyanostilbenes, (E)- and (Z)-2,3-Me(MeO)C6H3CH:CHC6H2(CN)(OMe)Me-3,5,4. Reduction of this mixture gave the diarylethane, which failed to undergo oxidative aryl-aryl cyclization. Photocyclization of the stilbenes gave a 7:1 mixture of phenanthrenes in which the unwanted 7-cyano regioisomer predominated. The Ziegler modification of the Ullmann coupling was used to prepare the sym. dialdehyde II, which underwent successive Wittig reaction with Ph3P:CH2 and hydride reduction to give the key intermediate III. Photocyclization of III gave a dihydrophenanthrene alc. which underwent successive oxidation to an aldehyde, Wittig condensation with Ph3P:CH2, and demethylation to give I. The overall yield of I from 2-methyl-3-methoxybenzaldehyde is 18% over 10 steps; the route provides the first total synthesis of this natural product. The experimental part of the paper was very detailed, including the reaction process of (3-Methoxy-2-methylphenyl)methanol(cas: 33797-34-1Formula: C9H12O2)
(3-Methoxy-2-methylphenyl)methanol(cas: 33797-34-1) belongs to ethers. Ethers lack the hydroxyl groups of alcohols. Formula: C9H12O2 Without the strongly polarized O―H bond, ether molecules cannot engage in hydrogen bonding with each other.
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem