2174-64-3

5-Methoxyresorcinol was used in synthesis of isorobustin, substituted linear and angular benzofurocoumarins.

ChEBI: Flamenol is a member of the class of resorcinols that is phloroglucinol in which one of the phenolic hydrogens has been replaced by a methyl group. It has a role as a Brassica napus metabolite. It is a member of resorcinols and a monomethoxybenzene. It is functionally related to a phloroglucinol.

Anhydrous phloroglucinol (25g,0.198 mole) is dissolved in absolutemethyl alcohol (100 ml) and the solution cooled to 18°.Dry hydrogenchloride gas is passed through the solution for 25 min at such a rate thatthe solution does not get saturated (approx. 200 bubbles/min).Themixture is then refluxed for 15 min，cooled immediately to 18° and dryhydrogen chloride gas passed again for25 min. The reaction mixture isallowed to stand for 12 hr and the solvent is removed by distillation invacuo.Great care is taken to remove as much of the solvent as possiblewithout applying any heat (preferably in rotatory evaporator).The residueis poured into water (500 ml) and extracted with ether (4 × 75 ml). The ether solution is dried (anhydrous sodium sulphate) and then distilled.The residual oily product is distilled in vacuo. A small quantity ofo-dimethyl phloroglucinol (5g,16.4 %) distils over first at 185-190°/25 mm and then o-monomethyl phloroglucinol (15g,54.2%) distils over at210° as a viscous oil. The viscous oil solidifies on standing for 2-3 days.M.p.78°.The yields are not consistent and vary according to the extent ofsaturation.