51591-52-7

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 2300, 1988 DOI: 10.1021/jo00245a031

InChI:InChI=1/C10H12O3/c1-8(7-11)13-10(12)9-5-3-2-4-6-9/h2-6,8,11H,7H2,1H3

Upstream product

• 2568-25-4 4-methyl-2-phenyl-1,3-dioxolane 
• 57-55-6 propylene glycol 
• 3277-27-8 diethyl benzoylphosphonate 
• 54769-36-7 N-benzoyloxybenzotriazole 
• 98-88-4 benzoyl chloride 
• 94-36-0 dibenzoyl peroxide 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 128733-25-5 Benzoic acid 2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl ester 
• 124-38-9 carbon dioxide 
• 100-47-0 benzonitrile 
• 75-56-9 methyloxirane 
• 108-32-7 1,2-propylene cyclic carbonate 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 60011-15-6 2-(benzoyloxy)propanoic acid 

Relevant academic research and scientific papers

Fast Addition of s-Block Organometallic Reagents to CO2-Derived Cyclic Carbonates at Room Temperature, Under Air, and in 2-Methyltetrahydrofuran

Fast addition of highly polar organometallic reagents (RMgX/RLi) to cyclic carbonates (derived from CO2 as a sustainable C1 synthon) has been studied in 2-methyltetrahydrofuran as a green reaction medium or in the absence of external volatile organic solvents, at room temperature, and in the presence of air/moisture. These reaction conditions are generally forbidden with these highly reactive main-group organometallic compounds. The correct stoichiometry and nature of the polar organometallic alkylating or arylating reagent allows straightforward synthesis of: highly substituted tertiary alcohols, β-hydroxy esters, or symmetric ketones, working always under air and at room temperature. Finally, an unprecedented one-pot/two-step hybrid protocol is developed through combination of an Al-catalyzed cycloaddition of CO2 and propylene oxide with the concomitant fast addition of RLi reagents to the in situ and transiently formed cyclic carbonate, thus allowing indirect conversion of CO2 into the desired highly substituted tertiary alcohols without need for isolation or purification of any reaction intermediates.

Benzoxaborole Catalyst for Site-Selective Modification of Polyols

The site-selective modification of polyols bearing several hydroxyl groups without the use of protecting groups remains a significant challenge in synthetic chemistry. To address this problem, novel benzoxaborole derivatives were designed as efficient catalysts for the highly site-selective and protecting-group-free modification of polyols. To identify the effective substituent groups enhancing the catalytic activity and selectivity, a series of benzoxaborole catalysts 1a–k were synthesized. In-depth analysis for the substituent effect revealed that 1i–k, bearing multiple electron-withdrawing fluoro- and trifluoromethyl groups, exhibited the greatest catalytic activity and selectivity. Moreover, 1i-catalyzed benzoylation, tosylation, benzylation, and glycosylation of various cis-1,2-diol derivatives proceeded with good yield and site-selective manner.

COMPOUNDS AND COMPOSITIONS FOR OCULAR DELIVERY

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Stannous chloride as a low toxicity and extremely cheap catalyst for regio-/site-selective acylation with unusually broad substrate scope

This work reports stannous chloride (SnCl2)-catalyzed regio-/site-selective acylation with unusually broad substrate scope. In addition to 1,2- and 1,3-diols and glycosides containing cis-vicinal diol, the substrate scope also includes glycosides without cis-vicinal diol. For such a substrate scope, usually, only methods using stoichiometric amounts of organotin reagents can lead to the same protection pattern with high selectivities and highly isolated yields (84-97% in most cases). Therefore, SnCl2, as a low toxicity and extremely cheap reagent, should be the best catalyst for regio-/site-selective acylation compared with any previously reported reagents. This journal is

Domino Two-Step Oxidation of β-Alkoxy Alcohols to Hemiacetal Esters: Linking a Stoichiometric Step to an Organocatalytic Step with a Common Organic Oxidant

Primary and secondary β-alkoxy alcohols can be cleanly and efficiently oxidized into hemiacetal esters in a cascade two-step process. mCPBA serves both as a stoichiometric oxidant in the first TEMPO-catalyzed step, converting alcohols to aldehydes/ketones, and as a reagent in the second Baeyer–Villiger stoichiometric oxidation, transforming the aldehydes/ketones into hemiacetal esters. The use of an oxidant common to both steps enables the domino reaction to proceed under a single experimental setting. Longer oxidative cascade sequences are possible when this new methodology is applied to suitable substrates.

Palladium on Carbon-Catalyzed Chemoselective Oxygen Oxidation of Aromatic Acetals

The development of an unprecedented chemoselective transformation has contributed to forming a novel synthetic process for target molecules. Chemoselective oxidation of aromatic acetals has been accomplished using a reusable palladium on carbon catalyst under atmospheric oxygen conditions to form ester derivatives with tolerance of aliphatic acetals and ketals.

Propylene carbonate synthesis from propylene glycol, carbon dioxide and benzonitrile by alkali carbonate catalysts

The synthesis of propylene carbonate from propylene glycol and carbon dioxide in the presence of various catalysts has been reported. Benzonitrile has been used as both solvent and dehydrating agent. Under optimal conditions, the best results were obtained in the presence of alkali carbonate catalysts. The propylene carbonate yield could reach up to 20% with a propylene-1,2-glycol conversion of 44%.

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Lipase-catalyzed alcoholysis of diol dibenzoates: Selective enzymatic access to the 2-benzoyl ester of 1,2-propanediol and preparation of the enantiomerically pure (R)-1-O-benzoyl-2-methylpropane-1,3-diol

Enzymatic debenzoylation of 1,2-propanediol dibenzoate with 1-octanol has been studied in organic solvent using lipases from different sources. In general a slow, highly regioselective alcoholysis in diisopropyl ether affords exclusively a monoester benzoylated at the secondary hydroxy group although the reaction proceeds with low enantioselectivity. In the presence of Pseudomonas cepacia lipase absorbed onto celite, a faster reaction allows the preparation of the 2-benzoyl ester of (R)-1,2-propanediol (82% ee) and the enantiomerically pure (R)-1-O-benzoyl-2-methylpropane-1,3-diol (>98% ee).

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The direct monoacylation of diols by acyl phosphate monoesters in water is a biomimetic analogy to the enzymic aminoacylation of tRNA by aminoacyl adenylates. Without catalysis, acyl phosphate monoesters react rapidly with amines but very slowly with water and alcohols. Lanthanide ions dramatically and selectively facilitate the base-catalyzed monoacylation of diols in water by methyl benzoyl phosphate (MBP), a typical acyl phosphate monoester, in neutral solutions where reactive amines are protonated and unreactive. The reaction patterns and reactivity of various diols with MBP in the presence of lanthanides are consistent with a mechanism that involves internal addition from the conjugate base of the bis-bidentate complex of the lanthanide with the diol and MBP. The method is also applicable to reactions of nucleosides as evidenced by the selective monoacylation of the 2′- or 3′-hydroxyl group of adenosine, without reaction of the 5′-hydroxyl group or the 6-amino group. Analogues of adenosine without the diol are unreactive. This suggests that the method will selectively monoacylate the hydroxyl groups at the unique diol in tRNA that forms the 3′-terminus.