| Identification | More | [Name]
Fructone | [CAS]
6413-10-1 | [Synonyms]
APPLINAL
ETHYL 2-(2-METHYL-1,3-DIOXOLAN-2-YL)ACETATE
ETHYL-2-METHYL-1,3-DIOXOLANE-2-ACETATE
ETHYLACETOACETATEETHYLENEGLYCOL-ACETAL
ETHYLACETOACETATE ETHYLENE GLYCOL KETAL
ETHYLACETOACETATE ETHYLENE KETAL
ETHYL METHYL DIOXOLANE ACETATE
FRUCTONE
KETOPOMMAL
1,3-Dioxolane-2-acetic acid, 2-methyl-, ethyl ester
1,3-Dioxolane-2-aceticacid,2-methyl-,ethylester
2-methyl-1,3-dioxolane-2-aceticacidethylester
3-dioxolane-2-aceticacid,2-methyl-ethylester
Ethyl (2-methyl-1,3-dioxolan-2-yl)acetate
Ethyl acetoacetate 3-ethylene acetal
Ethyl acetoacetate ethylene acetal
ethyl3-oxobutyrateethyleneketal
KETOPOMMAL (ETHYL METHYL DIOXALAN ACETATE)
METHYL DIOXALAN (FRUCTON)
FRUCTONE 95% | [EINECS(EC#)]
229-114-0 | [Molecular Formula]
C8H14O4 | [MDL Number]
MFCD00152488 | [Molecular Weight]
174.19 | [MOL File]
6413-10-1.mol |
| Hazard Information | Back Directory | [Chemical Properties]
Ethyl (2-Methyl-[1,3]dioxolan-2-yl)-acetate is not found in nature. It is a colorless liquid, d204
1.084–1.092, n20D 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. | [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, cm?1) 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 |
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