1144-50-9

Basic information

• Product Name: 3-Oxobutyric acid menthyl ester
• Synonyms: 3-Oxobutanoic acid 2-isopropyl-5-methylcyclohexyl ester;3-Oxobutyric acid 2-isopropyl-5-methylcyclohexyl ester;3-Oxobutyric acid menthyl ester;Acetoacetic acid 2-isopropyl-5-methylcyclohexyl ester;Acetoacetic acid p-menthan-3-yl ester
• CAS NO: 1144-50-9
• Molecular Formula: C₁₄H₂₄O₃
• Molecular Weight: 240.3386
• Mol File: 1144-50-9.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 308.5°Cat760mmHg
• Flash Point: 129.9°C
• Appearance: /
• Density: 0.98g/cm³
• Vapor Pressure: 0.000678mmHg at 25°C
• Refractive Index: 1.459
• CAS DataBase Reference: 3-Oxobutyric acid menthyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Oxobutyric acid menthyl ester(1144-50-9)
• EPA Substance Registry System: 3-Oxobutyric acid menthyl ester(1144-50-9)

Safety Data

• Hazardous Substances Data: 1144-50-9(Hazardous Substances Data)

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 
• 105-45-3 acetoacetic acid methyl ester 
• 1694-31-1 tert-butyl acetoacetate 
• 3666-82-8 2-benzyl-3-oxo-butyric acid methyl ester 
• 3623-52-7 isomenthol 
• 15356-70-4 menthol 
• 490-99-3 DL-neomenthol 

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 articles and documents

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.

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.

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.

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.