Synthesis Of Benzylic Alcohols Research Articles

Synthesis of Benzylic Alcohols by Decarboxylative Hydroxylation.

Herein, we demonstrate an efficient method for the decarboxylative hydroxylation of carboxylic acids with silver(I) as the catalyst and cerium ammonium nitrate as the oxidant and its utility in chemoselective late-stage functionalization of natural products and drug molecules. The chemoselectivity of this protocol arises from a benzylic nitrate intermediate that retards further oxidation and is hydrolyzed to the final benzylic alcohol product. Mechanistic investigation reveals that the facile oxidation of silver carboxylate affords silver(II) species as an intermediate oxidant responsible for decarboxylation.

The synthesis of benzyl alcohol: process optimization, photo-illuminated liquid phase hydrogenation, the improved green catalysts from natural zeolite

The synthesis of benzyl alcohol: process optimization, photo-illuminated liquid phase hydrogenation, the improved green catalysts from natural zeolite

Experimental and density functional theory studies on hydroxymethylation of phenylboronic acids with paraformaldehyde over a RhPPh3 catalyst

The synthesis of benzyl alcohols (BAs) is highly vital for their wide applications in organic synthesis and pharmaceuticals. Herein, BAs was efficiently synthesized via hydroxymethylation of phenylboronic acids (PBAs) and paraformaldehyde over a simple RhPPh3 catalyst combined with an inorganic base (NaOH). A variety of BAs with the groups of CH3−, CH3O−, Cl−, Br−, and so on were obtained with moderate to good yields, indicating that the protocol had a good universality. Density functional theory (DFT) calculations proposed the Hayashi‐type arylation mechanism involved the arylation step of PBA and Rh(OH)(PPh3)2 catalyst to form Rh(I)‐bound aryl intermediates and the hydrolysis step of Rh(I)‐bound aryl intermediates and HCHO to generate BA product (the rate‐determining step). The present route provides a valuable and direct method for the synthesis of BAs and expands the application range of paraformaldehyde.

ChemInform Abstract: Direct, Metal‐Free Synthesis of Benzyl Alcohols and Deuterated Benzyl Alcohols from p‐Toluenesulfonylhydrazones Using Water as Solvent.

AbstractMicrowave‐assisted synthesis of benzyl alcohols from various hydrazones is possible in water with high yields within a short times.

Synthesis of benzyl alcohol by indirect electrochemical catalyzed oxidation of toluene in basic methanol solvent

Benzyl alcohol detected by gas chromatography/mass spectrometry was obtained in high yields (78.3%) from the electrolysis of toluene at constant current intensity in basic methanol. The effect of the medium was investigated by UV spectrum. A possible reaction mechanism was proposed.

Alkylation of Benzene with Formaldehyde over ZSM-5

Benzyl alcohol is currently produced by hydrolysis of benzyl chloride and the by-products are sodium chloride and carbon dioxide. A “green chemistry” route would be the direct synthesis from benzene and formaldehyde. Therefore, ZSM-5, a medium pore zeolite, was used to evaluate the potential of using shape selective catalysis to control the product distribution obtained by alkylation of benzene with formaldehyde. The restriction of the channels resulted in a synthesis of benzyl alcohol and benzylmethyl ether. Neither of these products is obtained with a Friedel–Crafts' catalyst, such as AlCl3, nor with HY zeolite. Temperature has an effect on benzene conversion, but essentially none on product distribution. Water increases the selectivity to benzyl alcohol but decreases the conversion. Modification of the zeolite with boric acid increases the selectivity to benzylmethyl ether and benzyl alcohol, while modification with phosphorus acid does not, which may be due to the formation of phosphorus acid in the reaction mixture.