Chemical Properties
Ethyl (2-Methyl-[1,3]dioxolan-2-yl)-acetate is not found in nature. It is a colorless liquid, d
2041.084–1.092, n
20D 1.431–1.435, with a strong, fruity, apple-like, slightly green
odor. It can be prepared by acetalization of ethyl acetoacetate with ethylene
glycol.
Very slightly soluble in water, soluble in alcohol and Propylene glycol, miscible with most perfume oils.
Uses
flavors and fragrances
Trade name
Fructone (IFF), Jasmaprunat (Symrise)
Synthesis
Ethyl acetoacetate (39.0 g, 0.3 mol), ethylene glycol (55.8 g, 0.9 mol), and toluene (200 mL) were added to a 250 mL three-necked, round-bottomed flask fitted with a mechanical stirrer, thermometer, Dean-Stark manifold, and reflux condenser tube. Subsequently, p-toluenesulfonic acid monohydrate (0.2 g, catalytic amount) was added as a catalyst. The reaction mixture was heated to reflux and the water generated during the reaction was removed via a Dean-Stark water separator. After completion of the reaction, the solvent was removed under reduced pressure by rotary evaporator. The residue was distilled under reduced pressure and the fractions with boiling points of 96-99 °C were collected to give 47.6 g of the colorless oily product malate in 91% yield. The infrared spectrum of the product (KBr pressed sheet, cm1) showed characteristic absorption peaks: 2984, 2890, 1736, 1370, 1049.
References
[1] Journal of Chemical Research - Part S, 1997, # 1, p. 26 - 27
[2] Journal of Organic Chemistry, 1989, vol. 54, # 15, p. 3625 - 3634
[3] Journal of Catalysis, 2000, vol. 196, # 2, p. 345 - 351
[4] Tetrahedron Letters, 2011, vol. 52, # 51, p. 7004 - 7007
[5] RSC Advances, 2016, vol. 6, # 47, p. 41404 - 41409
