Chemical Properties
Clear colorless to yellow liquid
Uses
3,5-Dimethoxytoluene (DMT) may be used in the synthesis of 3,5-dimethoxybenzoic acid by oxidation and 2-methoxy-6-methyl-1,4-benzoquinone by catalytic oxidation with hydrogen peroxide (H
2O
2)/methyltrioxorhenium (CH
3ReO
3) in dimethyl carbonate (DMC).
Uses
3,5-Dimethoxytoluene has been suggested for
use in perfume compositions as supporting
note for Oakmoss and Vetiver, and as a novel
note in Chypre, Fougere and Oriental fragrance types.
Definition
ChEBI: 3,5-dimethoxytoluene is a member of the class of toluenes that is toluene in which the hydrogens at positions 3 and 5 have been replaced by methoxy groups. It is the major scent compound of many rose varieties. It has a role as a fragrance and a plant metabolite. It is a member of toluenes and a member of methoxybenzenes.
Production Methods
3,5-Dimethoxytoluene can be produced from Orcinol in weak aqueous alkali
with Dimethylsulfate at controlled temperature.
Synthesis Reference(s)
Organic Syntheses, Coll. Vol. 6, p. 859, 1988
The Journal of Organic Chemistry, 70, p. 3275, 2005
DOI: 10.1021/jo050075r
General Description
3,5-Dimethoxytoluene (DMT) is a methoxylated phenolic derivative. It is reported to be one of the main constituent of the floral volatiles in different rose varieties. It has been biosynthesized from orcinol by two successive methylation catalyzed by
O-methyltransferases (OMTs). The features of its aerobic oxidation with metal/bromide catalysts have been investigated.
Synthesis
A solution of dry orcinol (14.2 g,0.115 mole) in dry anhydrous acetone(150 ml) containing anhydrous potassium carbonate (45 g) is refluxed withdimethyl sulphate (23.6 ml，31.46 g, 0.25 mole) for 4 hr. The dimethylsulphate is added in small lots of 5 ml. After refluxing, the solution isfiltered and the inorganic residue washed with hot acetone (2 x 25 ml).The combined acetone solution is distilled and the residue macerated withcrushed ice. It is extracted with ether, the ether extract dried (anhydroussodium sulphate) and distilled. Yield 14.2 g (81.6%).B.p.102° (8 mm)
