119718-90-0

Basic information

• Product Name: Butyl mandelate
• Synonyms: butyl mandelate
• CAS NO: 119718-90-0
• Molecular Formula: C12H16O3
• Molecular Weight: 208.25
• Mol File: 119718-90-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Butyl mandelate(CAS DataBase Reference)
• NIST Chemistry Reference: Butyl mandelate(119718-90-0)
• EPA Substance Registry System: Butyl mandelate(119718-90-0)

Safety Data

• Hazardous Substances Data: 119718-90-0(Hazardous Substances Data)

Upstream product

• 56535-98-9 2,5-diphenyl-[1,3]dioxolan-4-one 
• 71-36-3 butan-1-ol 
• 119718-86-4 (RS)-butyl O-acetylmandelate 
• 14007-02-4 butyl mandelate 
• 17199-29-0 (S)-Mandelic acid 
• 611-71-2 (R)-Mandelic Acid 
• 108-05-4 vinyl acetate 
• 611-71-2 MANDELIC ACID 
• 14758-41-9 2-Hydroxy-2-phenyl-1,1,1-tris-(phenylmercapto)-aethan 
• 62173-99-3 benzyl 2-hydroxy-2-phenylacetate 
• 2674-04-6 diphenyl cadmium 
• 6295-06-3 butyl glyoxalate 
• 1074-12-0 phenylglyoxal hydrate 
• 122-43-0 butyl phenylacetate 

Downstream Products

• 119656-72-3 (R)-mandelic acid n-butyl ester 
• 85805-89-6 (S)-butyl 2-acetoxy-2-phenylethanoate 
• 139012-78-5 (R)-(-)-butyl O-acetylmandelate 
• 5524-55-0 n-butyl 2-oxo-2-phenylacetate 
• 164386-47-4 (4S,6S)-6-((R)-Butoxycarbonyl-phenyl-methoxy)-4-phenyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 

Relevant articles and documents

Efficient acid-catalyzed conversion of phenylglyoxal to mandelates on flame-derived silica/Alumina

Amorphous, nonporous silica/alumina (SA) made by flame-spray pyrolysis (FSP) efficiently catalyzes the direct conversion of phenylglyoxal (PG) to alkyl mandelates. The SAs exhibited a turnover frequency more than an order of magnitude higher than dealuminated zeolite Y, which hitherto has been considered as the most active solid acid for this reaction. The free diffusion of PG to surface acid sites and rapid removal of mandelate products are proposed to be at the origin of the superior performance of SAs. The recyclability of the catalyst was tested in five repetitive runs and showed no significant loss of catalyst performance.

Fe2(SO4)3 · xH2O in synthesis: A new and convenient catalyst for the esterification of mandelic acid with alcohols

Treatment of various of alcohols with mandelic acid in the presence of a catalytic amount of Fe2(SO4)3 · xH2O to give the corresponding esters in good yields.

An efficient and convenient procedure for preparation of mandelates catalysed by TiO2/SO4/2- solid superacid

An easy and efficient synthesis of mandelates in excellent yields from mandelic acid with alcohols catalysed by TiO2/SO42- solid superacid.

Novel SO3H-functionalized polyoxometalate-based ionic liquids as highly efficient catalysts for esterification reaction

Three novel heteropolyanion-based Br?nsted acidic ionic liquids (BAILs), butane mono sulfoacid-functionalized 1,10-phenanthrolinum, butane mono and bis sulfoacid-functionalized 1,4-dimethylpiperazinium salts of phosphortungstate catalyst (PhBs1-PW, [PipBs1]3-PW and [PipBs2]3-(PW)2) were synthesized and well characterized with FTIR, 1H and 13C NMR, Electro-Spray Ionization Mass Spectrometry (ESI-MS), Elemental analysis (CHNS), EDX and TG analysis techniques. The esterification reactions of monocarboxylic acids with monohydric alcohols were carried out using these catalysts. The introduced catalysts present a self-separation performance after reaction, which can be easily recovered and quite steadily reused as confirmed by six-run recycling test. Moreover, bis sulfoacid-functionalized 1,4-dimethylpiperazinium salt of phosphortungstate showed the best catalytic performance among the prepared catalysts for the esterification reaction.

Exploiting Cofactor Versatility to Convert a FAD-Dependent Baeyer–Villiger Monooxygenase into a Ketoreductase

Cyclohexanone monooxygenases (CHMOs) show very high catalytic specificity for natural Baeyer–Villiger (BV) reactions and promiscuous reduction reactions have not been reported to date. Wild-type CHMO from Acinetobacter sp. NCIMB 9871 was found to possess an innate, promiscuous ability to reduce an aromatic α-keto ester, but with poor yield and stereoselectivity. Structure-guided, site-directed mutagenesis drastically improved the catalytic carbonyl-reduction activity (yield up to 99 %) and stereoselectivity (ee up to 99 %), thereby converting this CHMO into a ketoreductase, which can reduce a range of differently substituted aromatic α-keto esters. The improved, promiscuous reduction activity of the mutant enzyme in comparison to the wild-type enzyme results from a decrease in the distance between the carbonyl moiety of the substrate and the hydrogen atom on N5 of the reduced flavin adenine dinucleotide (FAD) cofactor, as confirmed using docking and molecular dynamics simulations.

Autoamplification-Enhanced Oxidative Kinetic Resolution of sec-Alcohols and Alkyl Mandelates, and its Kinetic Model

In this contribution, the new dynamic nonlinear effect in asymmetric catalysis is discussed, manifesting itself in the oxidative kinetic resolution (OKR) of racemic secondary benzylic alcohols and alkyl mandelates with H2O2 in the presence of chiral Mn-based catalyst, with the apparent selectivity factor (krel) of the resolution being nonconstant over the reaction course. Typically, the initial growth of krel is changed into decay at high conversions. In this contribution, we demonstrate the oxidative kinetic resolution of various substrates bearing sec-alcoholic moieties, with the krel varying in different manners with increasing substrate conversion. We also present the predictive kinetic model of OKR with participation of asymmetric autoamplification. The influence of substrate and catalyst structure, as well as solvents and additives, on the behavior of krel variation, is discussed.

Mandelic acid derived ionic liquids: synthesis, toxicity and biodegradability

A series of ten ionic liquids (ILs) was synthesised from the renewable resource mandelic acid. The ILs showed low antimicrobial activity towards the thirteen bacterial and twelve fungal strains they were screened against. A general trend of increasing bacterial toxicity in the order methyl ester 60% in 28 days), a series of biodegradation transformation products has been proposed based on the degradation of the ester/amide alkyl chain. This data has allowed for an assessment of the effect of IL structural features on toxicity and biodegradation, particularly allowing for a comparison to earlier work where additional oxygen atoms were present to facilitate biodegradation and attenuate toxicity. The mandelic acid derived ILs did not pass the Closed Bottle test (OECD 301D) and can be included in the rules of thumb for the design of biodegradable ILs.

Zirconocene-catalyzed direct (trans)esterification of acyl acids (esters) and alcohols in a strict 1:1 ratio under solvent-free conditions

A highly efficient way for the direct (trans)esterification of acyl acids (esters) and alcohols in a strict 1:1 ratio using a zirconocene complex (1, 1 mol%), a strong Lewis acid of good water tolerance, as a catalyst under solvent-free conditions has been developed. A wide range of acid and alcohol (esters) substrates undergo (trans)esterification to produce carboxylic ester motifs in moderate to good or excellent yields with good functional tolerance, such as that towards C-Br as well as CC and CC bonds. And complex 1 can be recycled six times without showing a significant decline in catalytic efficiency. It was demonstrated that cyclandelate, which is used to treat high blood pressure as well as heart and blood-vessel diseases, can be directly synthesized on a gram scale with 81% yield (6.70 g) using complex 1.

Chemoselective esterification of α-hydroxyacids catalyzed by salicylaldehyde through induced intramolecularity

A new, direct and chemoselective esterification of α-hydroxyacids was developed using a reversible covalent-binding strategy. By taking advantage of acetal chemistry, simple aldehydes can be used to efficiently catalyze the esterification of α-hydroxy carboxylic acids in the presence of β-hydroxyacid moieties or other carboxylic acids in amounts equal to or in excess of the alcohols. A diverse array of α-aryl, α-alkyl, α-heteroaryl, and functionalized α-hydroxyacids were smoothly esterified with 1° and 2° alcohols catalyzed by 10 mol% inexpensive and commercially available salicylaldehyde, furnishing the resultant esterification products in 83-95% yields after a simple basic aqueous workup to remove the unreacted hydroxyacids. In addition, the salicylaldehyde can be recovered through vacuum distillation or silica gel purification, thereby meeting the standards of green chemistry. A mechanistic study proved that the formation of covalent adduct III during our proposed catalytic cycle (Scheme 1A) is responsible for the real catalysis.

Chiral cobalt-catalyzed enantioselective aerobic oxidation of α-hydroxy esters

A chiral cobalt-catalyzed enantioselective aerobic oxidative kinetic resolution of (±)-α-hydroxy esters, using molecular oxygen as a sole oxidant, is reported and a maximum of selectivity factor (s) 31.9 was achieved with >99% enantiomeric excess for unreacted α-hydroxy esters.