69160-04-9

Upstream product

• 24190-11-2 (R)-2-methoxy-2-phenylpropionic acid methyl ester 
• 67-56-1 methanol 
• 98-83-9 isopropenylbenzene 
• 13448-80-1 methyl R-(-)-atrolactate 
• 3966-30-1 (R)-Atrolactic acid 

Downstream Products

• 7472-67-5 α-phenyl-α-methoxypropanoic acid 
• 84999-97-3 C₂₃H₃₀O₂ 
• 84999-98-4 C₂₂H₂₈O₂ 
• 84999-96-2 C₂₁H₂₆O₂ 
• 84999-99-5 C₂₂H₂₆O₂ 
• 84999-95-1 (2R)-2-methoxy-2-phenylpropyl (Z)-3-phenyl-1-butenyl ether 
• 84999-94-0 (R)-(-)-cinnamyl 2-methoxy-2-phenylpropyl ether 

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.

Stereoselective selenium catalyzed dihydroxylation and hydroxymethoxylation of alkenes

The selenium atom of the selenocysteine plays a crucial role in the reduction of peroxides. Herein we showed that, in the absence of a thiol cofactor, the same aminoacid efficiently catalyzed the dihydroxylation of carbon-carbon double bonds leading to the stereoselective formation of 1,2-diols at room temperature and in on water conditions. Alternatively, in the presence of methanol, the corresponding β-methoxyalcohol can be prepared. The stereoselectivity of the reaction will be discussed and NMR evidences of the actual catalyst are here reported.

A general synthesis of 2-alkoxy-2-phenylpropanoic acids

A preparation of a variety of 2-alkoxy-2-phenylpropanoic acids in two steps is described. Epoxidation of α-methylstyrene with mCPBA in methanol or primary alcohol solvents proceeded with an acid-catalyzed in situ ring opening reaction to give the corresponding 2-alkoxy-2-phenyl-1-propanols in 28-91% yield. Lower yields were realized with secondary (22-58%) and tertiary (14%) alcohols. These alcohols were cleanly oxidized to the corresponding carboxylic acids using a mild Heyns' oxidation (O2, Pt/C) in generally good to excellent yields (25-92%). The derived (S)-α-methylbenzylamide diastereomers are nearly all well separated by capillary GC, and the use of this method to determine the enantiomeric purity of brucine-resolved 2-methoxy-2-phenylpropanoic acid was demonstrated.

The mechanism of the double bond cleavage in the titanium zeolite-catalvzed oxidation of α-methylstyrene by hydrogen peroxide: The β-hydroperoxy alcohol as intermediate

It is unequivocally shown that acetophenone, an oxidation product in the titanium zeolite-catalyzed oxidation of α-methylstyrene, derives from 2-hydroperoxy-2-phenyl-l-propanol as intermediate, which was detected and isolated in this reaction for the first time. VCH Verlagsgesellschaft mbH, 1996.

A NEW AND EFFECTIVE ASYMMETRIC SYNTHESIS OF 3-PHENYLALKANALS

Highly optically active 3-phenylalkanals were obtained by the reaction of alkyl halides and a chiral homoenolate equivalent derived from the cinnamyl ether 3 and potassium diisopropylamide, followed by acidic hydrolysis.