88416-64-2

Usage

InChI:InChI=1/C10H14O2/c1-8-3-5-9(6-4-8)10(2,12)7-11/h3-6,11-12H,7H2,1-2H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 65143-37-5 2-oxo-2-(4-tolyl)ethyl acetate 
• 4079-54-3 2-hydroxy-1-p-tolyl-ethanone 
• 42432-27-9 p-methyl-α-methylstyrene oxide 
• 1195-32-0 1-methyl-4-isopropenylbenzene 
• 106-38-7 para-bromotoluene 
• 116-09-6 hydroxy-2-propanone 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 67-56-1 methanol 
• 122-00-9 para-methylacetophenone 

Downstream Products

• 33596-66-6 2-(4-methylphenyl)propanal 
• 139906-46-0 (+/-)-1-acetoxy-2-(p-tolyl)-2-propanol 
• 122-00-9 para-methylacetophenone 

Relevant academic research and scientific papers

Photo-Induced Dihydroxylation of Alkenes with Diacetyl, Oxygen, and Water

Herein reported is a photo-induced production of vicinal diols from alkenes under mild reaction conditions. The present dihydroxylation method using diacetyl (= butane-2,3-dione), oxygen, and water dispenses with toxic reagents and intractable waste generation.

A Highly Regioselective Palladium-Catalyzed O,S Rearrangement of Cyclic Thiocarbonates

This work describes an operationally simple catalytic synthesis of cyclic S-thiocarbonates with predictable regioselectivity in good yields. The reaction utilizes substrates derived from ubiquitous 1,2-diols in an atom economical intramolecular rearrangement, catalysed by an inexpensive and simple catalyst–ligand system. A crystal structure is presented that clearly confirms the regioselectivity of the reaction.

A simple primary amine catalyst for enantioselective α-hydroxylations and α-fluorinations of branched aldehydes

A new primary amine catalyst for the asymmetric α-hydroxylation and α-fluorination of α-branched aldehydes is described. The products of the title transformations are generated in excellent yields with high enantioselectivities. Both processes can be performed within short reaction times and on gram scale. The similarity in results obtained in both reactions, combined with computational evidence, implies a common basis for stereoinduction and the possibility of a general catalytic mechanism for α-functionalizations. Promising initial results in α-amination and α-chlorination reactions support this hypothesis.

Resolution of diols via catalytic asymmetric acetalization

A highly enantioselective kinetic resolution of diols via asymmetric acetalization has been achieved using a chiral confined imidodiphosphoric acid catalyst. The reaction is highly efficient for the resolution of tertiary alcohols, giving selectivity factors of up to >300. Remarkably, even in cases where the selectivity factors are only moderate, highly enantioenriched diols are obtained via a stereodivergent resolution to diastereomeric acetals.

Homogeneous catalytic oxidation of styrene and styrene derivatives with hydrogen peroxide in the presence of transition metal-substituted polyoxotungstates

The tetrabutylammonium (TBA) salts of the Keggin-type polyoxotungstates with general formula [XW11M(H2O)O39](n-m)-, where X = P, B or Si and M = Mn, Fe or Co, were evaluated as catalysts in the oxidation of styrene, α-methylstyrene, p-methylstyrene, α,p-dimethylstyrene, p-chlorostyrene, p-nitrostyrene, and p-methoxystyrene under mild conditions, using aqueous H2O2 as an eco-sustainable oxidant. In this study, the influence of the catalysts and of the different styrene substituents on the oxidation reaction profile was evaluated in terms of conversion and selectivity. For all the performed catalytic studies, the main product results from the oxidative cleavage of the vinyl double bond, except in the case of the oxidation of p-methoxystyrene catalysed by BW11Mn, for which p-methoxyphenol is the main product. The catalysts BW11Mn and SiW11Co give rise to 100% conversion for almost all of the substrates, excluding p-methoxystyrene and p-nitrostyrene for both catalysts and α,p-dimethylstyrene only in the case of BW11Mn. The selectivity for C=C cleavage products resulting from the oxidative cleavage of the vinyl double bond can be as high as 98%, reaching 98% conversion for p-nitrostyrene when SiW11Co was used as a catalyst. Possible pathways are discussed and the oxidation of a few presumed intermediates was carried out. The systematic study of several substituted styrene derivatives suggests a possible reactivity order for these compounds in the catalytic system considered.

Homogeneous and heterogeneous photoredoxcatalyzed hydroxymethylation of ketones and keto esters: Catalyst screening, chemoselectivity and dilution effects

The homogeneous titanium- and dye-catalyzed as well as the heterogeneous semiconductor particle-catalyzed photohydroxymethylation of ketones by methanol were investigated in order to evaluate the most active photocatalyst system. Dialkoxytitanium dichlorides are the most efficient species for chemoselective hydroxymethylation of acetophenone as well as other aromatic and aliphatic ketones. Pinacol coupling is the dominant process for semiconductor catalysis and ketone reduction dominates the Ti(OiPr)4/methanol or isopropanol systems. Application of dilution effects on the TiO2 catalysis leads to an increase in hydroxymethylation at the expense of the pinacol coupling.

Lipase-catalyzed hydrolysis of some racemic 1-acetoxy-2-arylpropanes

Racemic 1-acetoxy-2-phenylpropane (12) and 1-acetoxy-2-(2- naphthyl)propane (33) were hydrolyzed with lipase at 35-36°C for 2 and 24 h to give predominantly (S)-2-phenyl-1-propanol (11) and (S)-2-(2-naphthyl)-1- propanol (32), respectively. However, racemic 1-acetoxy-2-(1-naphthyl)propane (25) was recovered intact even when the reaction was carried out for 240 h. On the other hand, the enantioselectivities towards racemic 2-phenyl (16), 2- (p-tolyl) (20), 2-(1-naphthyl) (28), and 2-(2-naphthyl) (36) derivatives of 1-acetoxy-2-propanol were very low.

Diastereofacial Controlled Addition Reaction of Alkoxymethylketones Modified by (2R,4R)-2,4-Pentanediol with Organometallics

Oxygen functionalized chiral alkoxymethylketone, derived from (2R,4R)-2,4-pentanediol, provided an efficient chiral environment in the reaction with organometallics which resulted in the either stereoselection depending on metal used; i.e., the reactions with MeLi and MeTi(OiPr)3 selectively furnished the corresponding (S)- and (R)-tertiary alcohols, respectively.