Preparation

synthesis of 3-methoxyphenol: The 1 mole of resorcinol is treated rapidly with stirring, in a three-necked flask provided with a reflux condenser, stirrer, internal thermometer, and dropping funnel, with 1.25 mole of 10% sodium hydroxide. With vigorous stirring, 1 mole of dimethyl sulfate is added in such a way that the temperature remains below 40° C (water cooling). To complete the reaction and to destroy unchanged dimethyl sulfate, the mixture is then heated for 30 min on a boiling water bath. After cooling, the organic layer is separated off and the aqueous solution is extracted several times with ether. The combined organic phases are washed with dilute sodium carbonate and then with water, dried with calcium chloride, and fractionated. Unchanged resorcinol can be recovered by acidifying the aqueous reaction solution and the wash water and extracting them with ether. The yield of 3-methoxyphenol is 50%, b.p. 113-115 °C/5 mm; b.p. 144°C/25mm; n20/D 1.552; d=1.131 g/mL at 25 °C. Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 206-207, (1973)

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by skin contact. Human systemic effects by inhalation: muscle weakness, headache, and irritabdtty. Human female reproductive effects by inhalation: menstrual cycle changes and dsorders. A severe eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes. See also ETHERS.

Definition

ChEBI: 3-methoxyphenol is a member of the class of phenols that is phenol having a methoxy-substituent at the 3-position. It is a member of phenols and a monomethoxybenzene. It derives from a resorcinol.

General Description

3-Methoxyphenol is a phenolic aroma compound typically present in food and beverage products.