1144-50-9

Usage

InChI:InChI=1/C14H24O3/c1-9(2)12-6-5-10(3)7-13(12)17-14(16)8-11(4)15/h9-10,12-13H,5-8H2,1-4H3

Upstream product

• 89-78-1 menthol 
• 141-97-9 ethyl acetoacetate 
• 674-82-8 4-methyleneoxetan-2-one 
• 3623-52-7 isomenthol 
• 15356-70-4 menthol 
• 490-99-3 DL-neomenthol 
• 3666-82-8 2-benzyl-3-oxo-butyric acid methyl ester 
• 1694-31-1 tert-butyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 

Downstream Products

• 117654-51-0 4-(2-Difluoromethoxy-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid bis-(2-isopropyl-5-methyl-cyclohexyl) ester 
• 166584-28-7 Co(C₁₄H₂₃O₃)2 
• 165336-49-2 Cu(C₁₄H₂₃O₃)2 

Relevant academic research and scientific papers

A facile and selective synthesis of β-keto esters via zeolite catalysed transesterification

Crystalline microporous aluminosilicates (zeolites) efficiently catalyse the transesterification of β-keto esters with high selectivity under environmentally safe reaction conditions.

Metal salts as novel catalysts for efficient transesterification of β-ketoesters

Ethyl/methyl β-ketoesters with alcohols in presence of catalytic amount of anhydrous metal salts (FeSO4, CuSO4) undergo smooth transesterification.

N, N’-dimethyl formamide (DMF) mediated Vilsmeier–Haack adducts with 1,3,5-triazine compounds as efficient catalysts for the transesterification of β-ketoesters

N, N’-dimethyl formamide (DMF) mediated Vilsmeier–Haack (VH) adducts with 1,3,5-triazine compunds such as trichloroisocyanuric acid (TCCA) and trichlorotriazine (TCTA) were prepared by replacing classical oxy chlorides POCl3, and SOCl2, which were explored as efficient catalysts for the transesterification of β-ketoesters. The prepared (TCCA/DMF) and (TCTA/DMF) adducts improved greenery of the classical Vilsmeier–Haack reagents (POCl3/DMF), and (SOCl2/DMF), and demonstrated their better efficient catalytic ativity. Reaction times were in the range: 3.5 to 6.5 hr (SOCl2/DMF); 2.8–5.2 hr (POCl3/DMF); 2.5–5.2 hr (TCCA/DMF) and 2.5–5.0 hr (TCTA/DMF) catalytic systems. Ultrasonically (US) assisted protocols with these reagents further reduced the reaction times (two to three times), while microwave assisted (MW) protocols with these reagents were much more effective. The reactions could be completed in only few seconds (less than a minute) in MWassisted protocols as compared to US assited reactions, followed by good product yields.

General and efficient transesterification of β-keto esters with various alcohols using Et3N as a br?nsted base additive

Transesterification of β-keto esters with a wide variety of allyl, benzyl, propargyl, and alkyl alcohols using, for the first time, commercially available and inexpensive Et3N as a Br?nsted base additive, is efficiently performed in toluene at reflux. The corresponding esters are exclusively obtained in 57-98% yields with no trace amounts of γ,δ-ketones, usually expected from the decarboxylative Carroll rearrangement.

Prussian blue as an efficient catalyst for rate accelerations in the transesterification of β-ketoesters

Prussian blue triggered transesterification of ethylacetoacetate with various alcohols underwent efficiently. The reaction is mild, eco-friendly, and selective with good yields. The proposed reaction pathway depicts the formation of an intermediate by the interaction of β-ketoesters with catalytic site of the Prussian blue, followed by nucleophilic attack of the alcohol at the electrophilic center followed by successive elimination of the proton to give the product. Observed longer reaction times under conventional conditions reduced amazingly under sonication and microwave irradiation followed enhanced yield of products.

Manganese(II) salts as efficient catalysts for chemo selective transesterification of β-keto esters under non-conventional conditions

Transesterification of β-ketoesters with various alcohols has been studied under conventional and non-conventional conditions using desktop chemicals such as Mn(II) salts as catalysts. These methods offered transesterification of β-ketoesters in good yields with dramatic rate accelerations and reduced reaction times. The developed protocols under nonconventional methods such as sonication and microwave irradiation are highly promising compared with the existing procedures.

Efficient trans-acetoacylation mediated by ytterbium(III) triflate as a catalyst under solvent-free condition

A simple and efficient trans-acetoacylation method for the synthesis of β-keto ester derivatives has been described using ytterbium(III) triflate as a new catalyst under solvent-free condition. This method was found to be efficient and convenient for the synthesis of a wide variety of β-keto ester derivatives.

Sustainable transesterification of β-ketoesters catalyzed by amine grafted on silica gel

Transesterification of β-ketoesters with various alcohols has been effected by N,N-diethylaminopropylated silica gel (NDEAP) as a catalyst in refluxing xylene. Generality of the reaction was demonstrated by successful transesterification of olefinic alcohols, tertiary alcohols and alcohols having acid- or base-sensitive substituents. The catalyst has been efficiently recycled more than five times without any re-activation.

Fluoroalkyldistannoxane Catalysts for Transesterification in Fluorous Biphase Technology

Novel, practical protocols of transesterification have been advanced with recourse to fluorous biphase technology. The fluoroalkyldistannoxane catalysts enable transesterification in FC-72 solvent to furnish 100% yields of the desired esters by use of reactants ester and alcohol in a 1:1 ratio. The catalysts also work in FC-72/organic solvent system as well as in toluene alone. A number of esters and alcohols bearing various functional groups are employable. The catalysts can be totally recovered and reused. More conveniently, the catalyst solution in FC-72 which is separated from the reaction mixture is directly used for the next reaction.

Transesterification of ketoesters using Amberlyst-15

A facile one-to-one transesterification of ketoesters by Amberlyst-15 is described.