Ethyl Levulinate

A mixture of 1 kg. (6.25 moles) of ethyl malonate, 540 g. (9.3 moles) of acetone, 800 g. (7.8 moles) of acetic anhydride, and 120 g. of fused zinc chloride is heated to reflux for 24 hours. To the cooled mixture is added 800 ml. of benzene, and the resulting solution is washed with four 500-ml. portions of water. The combined water washes are extracted with two 100-ml. portions of benzene, and the benzene extracts are washed with water and added to the main benzene solution. The benzene solution is distilled through a Vigreux column, and 1.2 kg. of crude ethyl isopropylidinemalonate is collected in the range 60-125°/18 mm. This material is redistilled through a 70 by 1.2 cm. Fenske column to give 411 g. of diethyl malonate, b.p. 81-83°/9 mm., and 654 g. (52%) of ethyl isopropylidinemalonate, b.p. 111-11379 mm., n2j5 1.4478..  

A mixture of 581 g. (5.0 moles) of levulinic acid, 583 ml. (10.0 moles) of 95% ethanol, 500 ml. of benzene, and 5 ml. of concentrated sulfuric acid is refluxed in an apparatus which provides for taking off the benzene-water-ethanol ternary azeotrope, condensing it, and returning the upper benzene layer continuously to the reaction vessel. A 15-hour reflux period is required to remove all the water in this 

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Ethylenedioxybutyl)-3-trichloro-acetamido-l-cyclohexene, 58, 9, 11 Ethylene glycol, 56, 44 Ethyl a-fluoro-l-naphthaleneacetate, 57, 73 Ethyl 2-fluoropropanoate, 57, 73 3-Ethylhexane, 58, 3, 4 3-ETHYL-l-HEXYNE, 58, 1, 2, 3, 4 Ethylidenecyclohexane, 59, 46 Ethyliodide, 59, 133 Ethyl 2-iodo-3-nitropropionate, 56,65 Ethyl isocyanide, 55, 98 Ethyl isocyanoacetate, 59,184 l-Ethyl-4-isopropylbenzene, 55,10 Ethyl levulinates, 5-substituted, 58, 81 ETHYL 2-METHYL1NDOLE-5CARBOXY-LATE, 56, 72... 

Ethyl levulinate was the only ketone which reacted with kojic acid in this manner, giving 4- 6-[5-hydroxy-2-(hydroxymethyl)-7-pyronyl] J -7-valerolactone (LXXIV) the addition was presumably followed by lactoni-... 

Ethyl levulinate, e236 Ethyl 3-methylcrotonate, el26... 

Oleksyszyn, J., Gruszecka, E., Kafarski, P., and Mastalerz, P., New phosphonic analogs of aspartic and glutamic acid by aminoalkylation of trivalent phosphorus chlorides with ethyl acetoacetate, ethyl levulinate and benzyl carbamate, Monatsh. Chem., 113, 59, 1982. 

Conversion of lignocellulose into transportation fuels via pyrolysis and subsequent oil upgrading [72], via gasification and subsequent Fischer-Tropsch or methanol synthesis [3], via hydrolysis and subsequent fermentation to ethanol or subsequent conversion into ethyl levulinate [45, 46, 73]. 

The submitters obtained 11.6 g (72%) of product starting from 18.4 g of (2-bromoallyl)diisopropoxyborane and 10.7 g of ethyl levulinate. The checkers obtained yields of 65-69% in runs on several different scales. 

Ethyl levulinate Pentanoic acid, 4-oxo-, ethyl ester (539-88-8), 75, 129 ( )-3-Ethyl-1-oxaspiro[3.5]nonan-2-one, 75, 119... 

SYNTHESIS OF 4-(2-BROMO-2-PROPENYL)-4-METHYL-v-BUTYRO-LACTONE BY THE REACTION OF ETHYL LEVULINATE WITH (2-BROMO-ALLYL)DIISOPROPOXYBORANE PREPARED BY HALOBORATION OF ALLENE... 

Ethyl levulinate, diisopropyl ether, and trifluoroacetic acid were purchased from Wako Pure Chemical Industries, Ltd., or Aldrich Chemical Company, Inc., and distilled before use. The checkers distilled diisopropyl ether from calcium hydride. 

Synthesis of 4-(2-Bromo-2-Propenyl)-4-Methyl-Y-Butyrolactone by the Reaction of Ethyl Levulinate with (2-Bromoailyl)diisopropoxyborane Prepared by Haloboration of Allene. 

Esters of 4-oxoacids, such as ethyl levulinate, can also be cyclized in the cold by treatment with hydrogen sulfide under acid conditions. An early report (39JCS1116) described the conversion of diethyl 2-acetylsuccinate (168) to ethyl 2-methyl-5-ethoxythiophene-3-carboxylate (169), by treatment with hydrogen sulfide in alcoholic HC1 at 0 °C. The reaction was reviewed in 1977 <77PS(3)377) a large number of 4-oxoesters (170) were subjected to the hydrogen sulfide treatment, and the products were carefully isolated and characterized. 

Ketones such as acetone, ethyl acctoaceiatc. ethyl levulinate or aceiylaceione react smoothly with ketene if a trace or sulfuric acid is present. The products are enol acetates of the ketones, acetnne giving rise lo isopropeny I acetate. 

Ethyl isonicotinate, e216 Ethyl isonipecotate, e206 Ethyl isopropylacetate, el 70 Ethyl isothiocyanatoformate, e32 Ethyl isovalerate, el 70 Ethyl levulinate, el 95 Ethyl linoleate, el 88... 

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