128733-39-1

Upstream product

• 626-95-9 1,4-Pentanediol 
• 70326-37-3 phenyl(2-thioxothiazolidin-3-yl)methanone 
• 31636-92-7 4-carbonylpentyl benzoate 
• 64-17-5 ethanol 
• 583-04-0 vinyl benzoate 
• 98-88-4 benzoyl chloride 
• 1071-73-4 5-Hydroxy-2-pentanone 

Downstream Products

• 82131-11-1 Benzoic acid 4-iodo-pentyl ester 
• 31636-92-7 4-carbonylpentyl benzoate 

Relevant academic research and scientific papers

Investigating the Influence of (Deoxy)fluorination on the Lipophilicity of Non-UV-Active Fluorinated Alkanols and Carbohydrates by a New log P Determination Method

Property tuning by fluorination is very effective for a number of purposes, and currently increasingly investigated for aliphatic compounds. An important application is lipophilicity (log P) modulation. However, the determination of log P is cumbersome fo

Catalytic Acceptorless Dehydrogenation of Aliphatic Alcohols

We developed the first acceptorless dehydrogenation of aliphatic secondary alcohols to ketones under visible light irradiation at room temperature by devising a ternary hybrid catalyst system comprising a photoredox catalyst, a thiophosphate organocatalyst, and a nickel catalyst. The reaction proceeded through three main steps: hydrogen atom transfer from the α-C-H bond of an alcohol substrate to the thiyl radical of the photo-oxidized organocatalyst, interception of the generated carbon-centered radical with a nickel catalyst, and β-hydride elimination. The reaction proceeded in high yield under mild conditions without producing side products (except H2 gas) from various alcohols, including sterically hindered alcohols, a steroid, and a pharmaceutical derivative. This catalyst system also promoted acceptorless cross-dehydrogenative esterification from aldehydes and alcohols through hemiacetal intermediates.

H-Bonding-promoted radical addition of simple alcohols to unactivated alkenes

H-Bonding-induced radical addition of simple alcohols to unactivated olefins was achieved. It effectively solved the long-standing problems of reactivity and selectivity in this type of reaction. The hydroxyalkylation occurred via site-specific cleavage of the α-hydroxyl-C-H bond in alcohols. This method allows a highly atom-economical, operationally simple and environmentally benign access to diverse primary, secondary and tertiary alcohols, diols, and even polyfluorinated alcohols. These useful chemicals are traditionally synthesized by using commercially unavailable organometallics via complex operations. In contrast, they can be facilely obtained through this protocol utilizing widely available starting materials.

Selective reduction of aldehydes and ketones to alcohols with ammonia borane in neat water

Chemoselective reduction of various carbonyl compounds to alcohols with ammonia borane (AB), a nontoxic, environmentally benign, and easily handled reagent, in neat water was achieved in quantitative conversions and high isolated yields. Interestingly, α- and β-keto esters were selectively reduced to corresponding hydroxyl esters by AB, while diols were obtained when sodium borohydride was used as a reducing agent. The procedure is also compatible with the presence of a variety of base-labile protecting groups, such as tosyl, acetyl, benzoyl, ester groups, and acid-labile protecting groups such as trityl and TBDMS groups, and others, such as the unsaturated double bond, nitro and cyano groups. Finally, a kilo scale reaction of methyl benzoylformate with AB was conducted in water and gave methyl mandelate in 94% yield.

A convenient and practical method for the selective benzoylation of primary hydroxyl groups using microwave heating

A convenient method for the selective protection of primary hydroxyl groups in 1,n diols is described. The use of microwave heating is shown to be advantageous.

Organotin-Mediated Monoacylation of Diols with Reversed Chemoselectivity: A Convenient Synthetic Method

The organotin-mediated monoesterification of unsymmetrical diols with reversed chemoselectivity has been explored to ascertain scope and limits of the method and to provide an easy and convenient synthetic procedure.The reaction has been performed on a set of substituted diols with some acylating agents usually employed as protecting groups.Two different procedures have been devised to obtain either the desired diol monoesters directly or the corresponding trialkylsilyl ethers as protected derivatives.The latter provides a convenient approach to the preparation of easily interconvertible diol monoesters.Also, the reaction has been optimized as a one-pot procedure, avoiding the isolation and purification of the stannylated intermediates.The reversed monoesterification method has been successfully applied to 1,2-, 1,3-, and 1,4-diols of primary-secondary, primary-tertiary, and secondary-tertiary types and to ether functions containing 1,2-diols.Within its limits, the described method represents the first direct one-pot monoesterification of diols at the most substituted site, allowing some remarkable achievements as (a) an almost regiospecific reversed monobenzoylation of some 1,2-diols, (b) the selective acylation of the tertiary hydroxyl of a primary-tertiary diol, and (c) a highly selective preparation of secondary pivalate of primary-secondary diols.