23985-59-3

Usage

Chemical Properties

slightly yellow crystalline powder

InChI:InChI=1/C11H14O3/c1-11(2,10(13)14)9(12)8-6-4-3-5-7-8/h3-7,9,12H,1-2H3,(H,13,14)/p-1/t9-/m1/s1

Upstream product

• 52178-65-1 ethyl 3-hydroxy-2,2-dimethyl-3-phenylpropanoate 
• 221675-86-1 3-acetoxy-2,2-dimethyldihydrocinnamic acid 
• 97-72-3 2-Methylpropionic anhydride 
• 100-52-7 benzaldehyde 
• 78-84-2 isobutyraldehyde 
• 97-62-1 Ethyl isobutyrate 
• 2052-01-9 2-bromo-2-methylpropionic acid 
• 23877-12-5 tert-butyl bromoisobutyrate 
• 79-31-2 isobutyric Acid 
• 31469-25-7 1,1-bis(trimethylsiloxy)-2-methylprop-1-ene 
• 60-29-7 diethyl ether 
• 141-52-6 sodium ethanolate 
• 7732-18-5 water 
• 20769-85-1 2-bromoisobutyric acid bromide 

Downstream Products

• 768-49-0 (2-methyl-1-propenyl)-benzene 
• 142777-11-5 3-bromo-2,2-dimethyl-3-phenyl-propionic acid 
• 23985-59-3 3-hydroxy-2,2-dimethyl-3-phenyl-propionic acid 
• 221675-86-1 3-acetoxy-2,2-dimethyldihydrocinnamic acid 
• 107627-85-0 3-hydroxy-2,2-dimethyl-3-phenyl-propionic acid-(2-diethylamino-ethyl ester) 
• 4412-08-2 3-methyl-2-phenylbut-2-enoic acid 
• 81158-98-7 3-Fluorosulfonyloxy-2,2-dimethyl-indan-1-ylidene-oxonium 
• 100-52-7 benzaldehyde 
• 85181-61-9 C₁₁H₁₁O⁽¹⁺⁾ 
• 32411-53-3 cis-5,5-dimethyl-6-phenyl-2-trichloromethyl-1,3-dioxan-4-one 
• 127852-67-9 (-)-(R)-3-hydroxy-2,2-dimethyl-3-phenylpropionic acid 
• 61914-40-7 (S)-2,2-dimethyl-3-hydroxy-3-phenylpropanoic acid 
• 124-38-9 carbon dioxide 
• 7732-18-5 water 

Relevant academic research and scientific papers

MNBA-mediated β-lactone formation: Mechanistic studies and application for the asymmetric total synthesis of tetrahydrolipstatin

Various β-lactones were prepared from β-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.

Chromium-mediated aldol and homoaldol reactions on solid support directed towards an iterative polyol strategy

Chromium-Reformatsky and chromium-homoaldol reactions run under neutral and mild reaction conditions. They are highly chemoselective, tolerant towards most common functional groups, and are not prone to retroaldol reactions. Initial studies directed to transfer these homogeneous chromium-mediated solution-phase reactions to solid phase are presented. The main objective was to develop a methodology to aid a combinatorial iterative strategy to polyols (polyketides) on solid phase. A general reactivity problem was observed with polystyrene based resins compared to the solution-phase reactions, independent if the electrophilic (aldehyde) or nucleophilic (bromide) end of the polyol chain was supported to the resin. A complicated penetration, or loss of the polar solvent environment after penetration into the resin, might be responsible for the reduced reactivity. Application of either a soluble polystyrene resin or a polystyrene resin with a polar polyethylene glycol tether resulted in improved yields.

Olefin Synthesis by Vanadium(V)-Induced Oxidative Decarboxylation-Deoxygenation of 3-Hydroxy Carboxylic Acids

Oxidative decarboxylation of 3-hydroxy carboxylic acids can be effected with various V(V) complexes.This process likely yields an intermediate 1,4-metalla diradical. β-elimination from this intermediate gives olefin and regenerates V(V), likely as VO2Cl.Thus, although the overall process involves no net change in oxidation state for vanadium, the decarboxylation process is oxidatively induced.Intramolecular trapping of the intermediate yields glycolate and then C-C cleavage products, and skeletal rearrangement gives ketonic products.Qualitatively, rates for oxidative decarboxylation of the acids and the stereospecificity of formation of olefinic products depend on the electron-withdrawing ability of groups attached to vanadium.Methodology is described for the preparation of tri- and tetrasubstituted olefins in high yield from appropriate 3-hydroxy carboxylic acid precursors.

KETENE BIS(TRIMETHYLSILYL) ACETALS. CROSS-ALDOL TYPE CONDENSATION REACTIONS WITH ALDEHYDES AND SCHIFF BASES

Condensation of the title acetals with aldehydes and Schiff bases in the presence of titanium tetrachloride is reported for the first time.It leads to β-hydroxyacids and to β-lactams via a cross-aldol type reaction, with good yields.

Preparation of trialkylsilyl ethers

In an improved catalytic process for preparing trialkylsilyl ethers from trialkylsilyl compounds and carbonyl group-containing compounds, the improvement consisting of using an organic or inorganic bifluoride (HF2?) as the catalyst.

1,2-Shift of a Carboxyl Group in a Wagner-Meerwein Rearrangement

On treatment with HSO3F in SO2Cl at 0 deg C, 3-hydroxy-2,2-dimethyl-3-phenylpropionic acid (1a) is trasformed into 2-phenyl-3-methyl-2-butenoic acid (2a) (isolated yield: 40-44percent).Using monolabelled -1a (1a*) and doubly labelled 2>-1a (1a**), the migration of HOOC (or a mechanistically equivalent group) was proved; a cross experiment established the intramolecular character of the rearrangement.By following the reaction at low temperature in an NMR. spectrometer, the formation of intermediates and side products was demonstrated.

Reaction de Reformatsky a froid avec des α-bromoesters-acetals. I. Une methode generale pour la synthese des β-hydroxyacides a partir des α-bromoesters de tetrahydropyrannyle (Note de laboratoire)

The readily accessible tetrahydropyranyl esters of α-bromoacids can be used in the Reformatsky reaction for the preparation of β-hydroxyacids.The reaction is generally carried out in cold tetrahydrofuran.The β-hydroxyacids can be easily obtained by stirring the cold solution of their tetrahydropyranyl esters with dilute hydrochloric acid.