135366-63-1

Basic information

• Product Name: ethyl α-acetyl-α-hydroxy-benzenepropanoate
• Synonyms: ethyl α-acetyl-α-hydroxy-benzenepropanoate
• CAS NO: 135366-63-1
• Molecular Weight: 236.268
• Mol File: 135366-63-1.mol

Chemical Properties

• CAS DataBase Reference: ethyl α-acetyl-α-hydroxy-benzenepropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl α-acetyl-α-hydroxy-benzenepropanoate(135366-63-1)
• EPA Substance Registry System: ethyl α-acetyl-α-hydroxy-benzenepropanoate(135366-63-1)

Safety Data

• Hazardous Substances Data: 135366-63-1(Hazardous Substances Data)

Upstream product

• 620-79-1 Ethyl 2-benzylacetoacetate 
• 34867-86-2 2,3-dioxaspiro[4.4]nonane-1,4-dione 

Relevant articles and documents

Mild air-oxidation of 1,3-dicarbonyl compounds with cesium salts: Novel α-hydroxylation accompanied by partial hydrolysis of malonate derivatives

1,3-Dicarbonyl compounds (1) were efficiently oxygenated at the α-position with cesium salts, such as CsF or Cs2CO3 (0.1 Meq) in DMF at room temperature. Reaction of malonate derivatives (1a, b) with excess amount (2 Meq) of Cs2

Nickel-catalyzed hydroxylation of 1,3-dicarbonyl compounds by dimethyldioxirane

Various 1,3-dicarbonyl compounds were directly hydroxylated by dimethyldioxirane, a preparative useful extension of this oxidation is the efficient catalysis by Ni(II) salts through chelation.

Lanthanide-catalyzed oxyfunctionalization of 1,3-diketones, acetoacetic esters, and malonates by oxidative C-O coupling with malonyl peroxides

The lanthanide-catalyzed oxidative C-O coupling of 1,3-dicarbonyl compounds with diacyl peroxides, specifically the cyclic malonyl peroxides, has been developed. An important feature of this new reaction concerns the advantageous role of the peroxide acti

Highly efficient C-H hydroxylation of carbonyl compounds with oxygen under mild conditions

A transition-metal-free Cs2CO3-catalyzed α-hydroxylation of carbonyl compounds with O2 as the oxygen source is described. This reaction provides an efficient approach to tertiary α-hydroxycarbonyl compounds, which are highly valued chemicals and widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very environmentally friendly and practical. This transformation is highly efficient and highly selective for tertiary C(sp3)-H bond cleavage. OH, so simple! A transition-metal-free Cs2CO 3-catalyzed α-hydroxylation of carbonyl compounds with O 2 provided a variety of tertiary α-hydroxycarbonyl compounds (see scheme; DMSO=dimethyl sulfoxide), which are widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very efficient and practical.

I2-catalyzed direct α-hydroxylation of β-dicarbonyl compounds with atmospheric oxygen under photoirradiation

An I2-catalyzed hydroxylation of β-dicarbonyl moieties using air as the oxidant under photoirradiation has been developed for the easy preparation of α-hydroxy-β-dicarbonyl compounds. The transformation was completed with only 1 mol % of I2. With α-unsubstituted malonates, the hydroxylated dimerization product was afforded as the predominant product along with a minor product, α,α-dihydroxyl malonate.

Oxidative iodination of carbonyl compounds using ammonium iodide and oxone

A simple, efficient, mild, and regioselective method for oxyiodination of carbonyl compounds has been reported by using NH4I as the source of iodine and Oxone as an oxidant. Various carbonyl compounds such as aralkyl ketones, aliphatic ketones (acyclic and cyclic), and β-keto esters proceeded to the respective α-monoiodinated products in moderate to excellent yields. Unsymmetrical aliphatic ketones reacted smoothly yielding a mixture of 1-iodo and 3-iodo ketones with the predominant formation of 1-iodoproduct.

Pd/C-catalyzed direct α-oxygenation of 1,3-dicarbonyl compounds using molecular oxygen

A hydroxyl group was readily and directly introduced into the α-position of a variety of β-dicarbonyl compounds by heterogeneous Pd/C-catalyzed oxygenation using molecular oxygen. Georg Thieme Verlag Stuttgart.

Preparation of acyloins by cerium-catalyzed, direct hydroxylation of β-dicarbonyl compounds with molecular oxygen

We report the metal-catalyzed α-hydroxylation of a variety of cyclic and acyclic β-dicarbonyl compounds by molecular oxygen. The decisive advantage of this new method is the use of catalytic amounts of the nontoxic cerium salt CeCl3·7H2O in 2-propanol at ambient temperature. Most of the cyclic substrates 4a-4i give high yields of analytically pure products 5a-5i, and the workup procedure is simple filtration through silica gel. The oxidation of acyclic dicarbonyl compounds 4j-4p, however, is accompanied by side reactions and decomposition, reducing the yields of products 5j-5p significantly. A proposed mechanism is in agreement with experimental results, in particular the observed oxygen uptake. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Highly Efficient Hydroxylation of Carbonyl Compounds with Dimethyldioxirane

The enolates and/or enols of ketones, esters, β-diketones, β-oxo esters, and β-oxolactones were transformed by dimethyldioxirane (isolated in acetone solution or generated in situ) into their α-hydroxy compounds in good to excellent yields.The direct hydroxylation of the enols was significantly enhanced by the use of fluoride ion.For the enolate of camphor the exo/endo diastereoselectivity depended significantly on the metal ligand; the highest exo/endo ratio (93:7) was observed for the enol trimethylsilyl ether of camphor.Key Words: Dimethyldioxirane / Enolates / Hydroxylation / α-Hydroxy carbonyl compounds / Enol silyl ethers