1070-35-5

Basic information

• Product Name: Pentanoic acid, 4-oxo-, 2-propenyl ester
• Synonyms: Pentanoic acid, 4-oxo-, 2-propenyl ester;Allyl levulinate
• CAS NO: 1070-35-5
• Molecular Formula: C₈H₁₂O₃
• Molecular Weight: 156.18
• Mol File: 1070-35-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pentanoic acid, 4-oxo-, 2-propenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Pentanoic acid, 4-oxo-, 2-propenyl ester(1070-35-5)
• EPA Substance Registry System: Pentanoic acid, 4-oxo-, 2-propenyl ester(1070-35-5)

Safety Data

• Hazardous Substances Data: 1070-35-5(Hazardous Substances Data)

Usage

InChI:InChI=1S/C8H12O3/c1-3-6-11-8(10)5-4-7(2)9/h3H,1,4-6H2,2H3

Upstream product

• 107-18-6 allyl alcohol 
• 123-76-2 levulinic acid 
• 106-95-6 allyl bromide 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 591-12-8 5-methyl-2-furanone 

Downstream Products

• 123-38-6 propionaldehyde 
• 123-76-2 levulinic acid 
• 140710-59-4 tert-butyldiphenylsilyl (1R^*,2S^*,3R^*)-2-(tert-butyldiphenylsiloxy)-3-(4-oxopentanoyloxymethyl)cyclobutane-1-carboxylate 

Relevant articles and documents

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Reaction of dicarbonates with carboxylic acids catalyzed by weak Lewis acids: General method for the synthesis of anhydrides and esters

The reaction between carboxylic acids (RCOOH) and dialkyl dicarbonates [(R1OCO)2O], in the presence of a weak Lewis acid such as magnesium chloride and the corresponding alcohol (R1OH) as the solvent, leads to the esters RCOOR1 in excellent yields. The mechanism involves a double addition of the acid to the dicarbonate, affording a carboxylic anhydride [(RCO)2O], R1OH and carbon dioxide. The esters arise from the attack of the alcohols on the anhydrides. Exploiting the lesser reactivity of tert-butyl alcohol in comparison with other alcohols, a clean synthesis of both carboxylic anhydrides and esters has been set up. In the former reaction, an acid/Boc2O molecular ratio of 2:1 leads to the anhydride in good to excellent yields, depending on the stability of the resulting anhydride to the usual workup conditions. In the latter reaction, stoichiometric mixtures of the acid and Boc2O are allowed to react with a twofold excess of a primary alcohol, secondary alcohol or phenol (R 2OH) to give the corresponding esters (RCOOR2). Purification of the products is particularly easy since all byproducts are volatile or water soluble. A very easy chromatography is required only in the case of nonvolatile alcohols. A broad variety of sensitive functional groups is tolerated on both the acid and the alcohol, in particular a high chemoselectivity is observed. In fact, no transesterification processes occur with the acid-sensitive acetoxy group and methyl esters. Georg Thieme Verlag Stuttgart.