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Cas Database

104-54-1

104-54-1

Identification

  • Product Name:Cinnamyl alcohol

  • CAS Number: 104-54-1

  • EINECS:203-212-3

  • Molecular Weight:134.178

  • Molecular Formula: C9H10O

  • HS Code:29062990

  • Mol File:104-54-1.mol

Synonyms:3-Phenyl-2-propenol;Phenyl-2-propen-1-ol;gamma.-Phenylallyl alcohol;Styrone;gamma-Phenylallyl alcohol;Styrylcarbinol;2-Propen-y1-ol, 3-phenyl-;2-Propen-1-ol, 3-phenyl-;Zimtalcohol;2-Propen-1-ol,3-phenyl-;3-Phenyl-2-propen-1-ol;Styryl alcohol;3-phenylprop-2-en-1-ol;Styryl carbinol;Propenoic acid, 3-phenyl-, (trans)-;3-Fenyl-2-propen-1-ol [Czech];1-Phenylprop-1-en-3-ol;Alkohol skoricovy [Czech];3-Phenylallyl alcohol;Cinnamic alcohol FCC;Cinnamic Alcohol , Natural;3-Phenyl 2-Propen-1-ol;cinnamic alcohol,cinnamyl alcohol;Cinnamic alcohol;Cinnamyl Alcohol, Cinnamic Alcohol;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. Absorption, Distribution and ExcretionCINNAMYL ALC IS EXCRETED UNCHANGED IN NEUTRAL EXTRACT WHEN GIVEN TO RATS.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
  • Product Description:Cinnamyl Alcohol
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  • Product Description:Cinnamyl alcohol
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  • Product Description:Cinnamyl alcohol analytical standard
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  • Product Description:Cinnamyl alcohol solution certified reference material, 2000?μg/mL in methanol, ampule of 1?mL
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  • Product Description:Cinnamyl alcohol natural,96%,FG
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  • Product Description:Cinnamyl alcohol ≥98%,FG
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Relevant articles and documentsAll total 463 Articles be found

Catalytic hydrosilylation of carbonyl compounds by hydrido thiophenolato iron(II) complexes

Xue, Benjing,Sun, Hongjian,Niu, Qingfen,Li, Xiaoyan,Fuhr, Olaf,Fenske, Dieter

, p. 23 - 28 (2017)

The hydrosilylation of aldehydes and ketones under mild conditions with hydrido thiophenolato iron(II) complexes [cis–Fe(H)(SAr)(PMe3)4] (1–4) as catalysts is reported using (EtO)3SiH as an efficient reducing agent in the yields up to 95%. Among them complex 1 is the best catalyst. Complex 1 could also be used as catalyst to reduce the α,β-unsaturated carbonyl compounds selectively to the α,β-unsaturated alcohols in high yields.

Chemoselective protection of hydroxyl groups and deprotection of silyl ethers

Bandgar,Kasture

, p. 1101 - 1104 (2001)

Trimethylsilylation of alcohols and phenols is carried out using hexamethyldisilazane and LiClO4 under microwave irradiation and neutral conditions. The deprotection of silyl ethers is carried out similarly using natural kaolinitic clay and a few drops of water.

Zn(BH4)2/ultrasonic irradiation: An efficient system for reduction of carbonyl compounds to their corresponding alcohols

Fanari, Siamak,Setamdideh, Davood

, p. 695 - 697 (2014)

Zn(BH4)2 under ultrasonic irradiation is an efficient reducing system in CH3CN. This system reduces a variety of carbonyl compounds to their corresponding alcohols at room temperature in high to excellent yields of the products. Also, a,b-unsaturated aldehydes and ketones was regioselectively reduced to the corresponding allylic alcohols.

Unexpected course of Wittig reaction when using cinnamyl aldehyde as a substrate

Szymczyk, Monika

, p. 264 - 266 (2017)

When trans-cinnamyl aldehyde was used as a substrate of the Wittig reaction, instead of the olefination product, formation of four products with (E)-1,3-diphenylprop-2-en-1-ol and cinnamyl alcohol was observed being quite unexpected ones. The possible mechanism of this unusual reaction has been considered.

Conversion of alkyl halides into the corresponding alcohols under mild reaction conditions

Ruddick, Clare L.,Hodge, Philip,Houghton, Mark P.

, p. 1359 - 1362 (1996)

Reaction of primary, cyclopentyl, allyl and arylmethyl halides, but not an acyclic secondary halide or a tertiary halide, in acetone or tetrahydrofuran with the formate form of a commercial anion exchange resin gave formate esters in good yields. The formates were hydrolysed efficiently to the corresponding alcohols by a brief treatment with hydrochloric acid. Reaction of primary alkyl bromides or iodides, secondary alkyl bromides, cinnamyl and arylmethyl halides in tetrahydropyran or 1,4-dioxane with the bicarbonate form of the same anion-exchange resin gave the corresponding alcohols directly in good yields. This latter reaction can be carried out successfully in the presence of ester or amide groups.

Reduction of carbonyl compounds to the corresponding alcohols with isopropanol on dehydrated alumina under microwave irradiation

Kazemi,Kiasat

, p. 2255 - 2260 (2002)

The reduction of different types of aldehydes and ketones were performed in the presence of isopropylalcohol (as solvent and hydride source) under microwave irradiation. It is proved that dehydrated Woelm chromatographic alumina supported KOH catalyses these transformations. Regioselectivity was observed in the reduction of cinnamaldehyde and chemoselectivity was observed in the reduction of carbonyl in the presence of nitro group.

Exclusive 1,2-reduction of functionalised conjugated aldehydes with sodium triacetoxyborohydride

Singh, Jasvinder,Sharma, Munisha,Kaur, Irvinder,Kad, Goverdhan L.

, p. 1515 - 1519 (2000)

Functionalised α,β-unsaturated aldehydes were exclusively reduced to allylic alcohols with sodium-triacetoxyborohydride. Neither saturated alcohol nor saturated aldehydes are obtained. Conjugated ketones are not reduced.

Pyrococcus furiosus-mediated reduction of conjugated carboxylic acids: Towards using syngas as reductant

Ni, Yan,Hagedoorn, Peter-Leon,Xu, Jian-He,Arends, Isabel W.C.E.,Hollmann, Frank

, p. 52 - 55 (2014)

Pyrococcus furiosus catalyzes the reduction of carboxylic acids to their corresponding alcohols. In addition to hydrogen also carbon monoxide can be used as stoichiometric reductant, paving the way to cheap syngas to promote biocatalytic acid reduction. The enzymes responsible for coupling CO-oxidation to acid reduction are currently unknown but may represent an unprecedented enzyme class. Furthermore, enoate reductase-like activity has been detected in P. furiosus while lacking 'classical' enoate reductases.

Core-shell AgNP@CeO2 nanocomposite catalyst for highly chemoselective reductions of unsaturated aldehydes

Mitsudome, Takato,Matoba, Motoshi,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi

, p. 5255 - 5258 (2013)

Selective silver: A core-shell AgNP-CeO2 nanocomposite (AgNP@CeO2) acted as an effective catalyst for the chemoselective reductions of unsaturated aldehydes to unsaturated alcohols with H2 (see figure). Maximizing the AgNP-CeO2 interaction successfully induced the heterolytic cleavage of H2, resulting in highly chemoselective reductions. Furthermore, a highly dispersed AgNP@CeO2 system was also developed that exhibited a higher activity than the original AgNP@CeO2. Copyright

SELECTIVITY IN THE ACID CATALYSED REDUCTION OF CARBONYL COMPOUNDS TO ALCOHOLS BY BIS(TRIPHENYLPHOSPHINE)COPPER(I) TETRAHYDROBORATE: REDUCTION OF ALDEHYDES IN THE PRESENCE OF KETONES

Fleet, G.W.J.,Harding, P.J.C.

, p. 675 - 678 (1981)

Bis(triphenylphosphine)copper(I) tetrahydroborate reduces carbonyl compounds to alcohols in the presence of acid catalysts in excellent yields with high stereoselectivity; α,β-unsaturated aldehydes are reduced regioselectively.In a mixture of an aldehyde and a ketone, an aldehyde may be reduced preferentially.

Pinacol coupling of aromatic aldehydes and ketones using TiCl 3-Al-EtOH under ultrasound irradiation

Li, Ji-Tai,Lin, Zhi-Ping,Qi, Na,Li, Tong-Shuang

, p. 4339 - 4348 (2004)

Titanium trichloride in EtOH can be reduced by Al to the corresponding low-valent titanium complexes. This can reduce some aromatic aldehydes and ketones to the corresponding pinacols in 40-82% yields within 30-90 min at r.t. under ultrasound irradiation.

A highly efficient Cu/AlOOH catalyst obtained by in situ reduction: Catalytic transfer hydrogenation of ML into Γ-GVL

Ma, Mingwei,Liu, Hui,Cao, Jingjie,Hou, Pan,Huang, Jiahui,Xu, Xingliang,Yue, Huijuan,Tian, Ge,Feng, Shouhua

, p. 52 - 60 (2019)

Catalytic transfer hydrogenation (CTH) of carbonyl compounds is considered as one of the most promising processes in the synthesis of fuels and chemicals. In this work, we propose a one-step strategy for catalyst preparation and CTH. Using the strategy, the production of γ-valerolactone (γ-GVL) was performed with isopropanol (2-PrOH) as solvent over in situ reduced nano-Cu/AlOOH catalyst from Cu2(OH)2CO3/AlOOH and the optimal reaction conditions for γ-GVL are 180 °C for 5 h using the in situ reduced catalyst with Cu/Al molar ratio 3/1 (90.51% yields of γ-GVL). Furthermore, it has been confirmed by different characterization methods (such as: SEM, TEM, XPS, etc.) that the catalyst is heterogeneous and exhibits high catalytic activity and stability which is attributed to the stability of the zero-valent copper in the catalyst and the nanosized particles of the catalyst. In addition, the catalysts also show general applicability to other carbonyl compounds.

A SIMPLE PROCEDURE FOR THE SYNTHESIS OF THREE-CARBON HOMOLOGATED BORONATE ESTERS AND TERMINAL ALKENES VIA NUCLEOPHILIC DISPLACEMENT IN α-HALOALLYLBORONATE ESTER

Brown, Herbert C.,Rangaishenvi, Milind V.

, p. 7115 - 7118 (1990)

The transfer reactions of α-haloallylboronate ester 1 with representative organolithium and Grignard reagents provide α-alkyl- or α-aryl-substituted allylboronate esters, readily converted into three-carbon homologated boronate esters and terminal alkenes.

Ultrasonic-promoted selective reduction of aldehydes vs. ketones by NaBH4/PhCO2Na/H2O

Mirtaghizadeh, Mina,Setamdideh, Davood

, p. 1539 - 1543 (2016)

In this study, we have investigated the selective reduction of aldehydes vs. ketones by NaBH4/PhCO2Na/H2O system under ultrasound irradiation. NaBH4 (1.25 equivalents) and PhCO2Na (2 equivalents) is optimized conditions for reduce a variety of aldehydes (1 mmol) in the presence of ketones (1 mmol) to their corresponding alcohols in water as green solvent in high to excellent yields of the product (90-95%). A benzoate-borane complex [PhCO2-H3B]Na is possibly the active reductant in the reaction mixture.

Cofactor recycling for selective enzymatic biotransformation of cinnamaldehyde to cinnamyl alcohol

Zucca, Paolo,Littarru, Maria,Rescigno, Antonio,Sanjust, Enrico

, p. 1224 - 1226 (2009)

The enzymatic, selective hydrogenation of cinnamaldehyde to cinnamyl alcohol is reported here. Yeast alcohol dehydrogenase was used in a substrate-coupled process with cofactor recycling. Both 100% selectivity and aldehyde conversion were achieved within

Preparation and Some Reactions of Allylic Indium Reagents

Araki, Shuki,Shimizu, Toshio,Johar, Perminder S.,Jin, Shun-Ji,Butsugan, Yasuo

, p. 2538 - 2542 (1991)

A variety of allylic indium sesquihalides were readily prepared by the reaction of indium powder with allylic halides in DMF at room temperature.Protonation of the allylindium reagents proceeded regiospecifically at the γ-position of the allylic group to give 1-propenes.A facile transformation of α-pinene to β-pinene was achieved via a myrtenylindium intermediate.Oxygenation of the allylic indium reagents gave mixtures of allylic alcohol isomers in moderate yields.The coupling of the allylindium reagents with cyclic imides gave diverse products depending on the structures of the substrates and the reagents.Stannylation with tributylchlorostannane occurred exclusively at the α-carbon, yielding allyltributylstannanes; E,Z isomerization of the allylic double bond depended largely upon the substitution pattern on the allylic moiety.

Poly(1,4-butyl-bis-vinylpyridinium) borohydride as a new stable and efficient reducing agent in organic synthesis

Khaligh, Nader Ghaffari

, p. 721 - 727 (2013)

The unstable sodium borohydride is stabilized on modified poly(4-vinylpyridinium), and it is used as an efficient and regenerable polymer-supported borohydride reagent for the reduction of a variety of carbonyl compounds, such as aldehydes, ketones, α,β-unsaturated carbonyl compounds, α-diketones and acyloins, in good to excellent yields.

Reduction of aldehydes catalyzed by oxo-rhenium(V) complexes containing heterocyclic ligands

Bernando, Joana R.,Florindo, Pedro R.,Wolff, Mariusz,Machura, Barbara,Fernandes, Ana C.

, p. 414 - 418 (2015)

This work describes the catalytic activity of several oxo-rhenium complexes containing the heterocyclic ligands 2-(2-hydroxy-5-methylphenyl)benzotriazole (Hhmpbta), 2-(2-hydroxyphenyl)benzothiazole (Hhpbt), 2-(2-hydroxyphenyl)benzoxazole (Hhpbo), 2-(2-hydroxyphenyl)-1H-benzimidazole (Hhpbi), isoquinoline-1-carboxylic acid (iqcH), and 4-methoxy-2-quinolinecarboxylic acid (mqcH) in the reduction of 4-nitrobenzaldehyde using phenylsilane as reducing agent. In general, all of the catalysts tested gave good to excellent yields of the 4-nitrobenzyl alcohol. Although, the best result was obtained with the catalytic system PhSiH3/[ReOBr2(hmpbta)(PPh3)] (5 mol %). This system was also applied to the reduction of a large variety of aldehydes, producing the corresponding primary alcohols in good to excellent yields and good chemoselectivity.

Quaternized amino functionalized cross-linked polyacrylamide as a new solid - Liquid phase transfer catalyst in reduction of carbonyl compounds with NaBH4

Tamami, Bahman,Mahdavi, Hossein

, p. 821 - 826 (2003)

Poly[N-(2-aminoethyl)acrylamido]trimethyl ammonium chloride resin was developed as a new polymeric phase transfer catalyst. This quaternized polyacrylamide catalyzed the chemoselective reduction of aldehydes and ketones by NaBH4 to give corresponding alcohols in high yields under mild conditions.

Metal-free catalytic reduction of aldehydes, ketones, aldimines, and ketimines

Matsuoka, Hiroaki,Kondo, Kazuhiro

, p. 1314 - 1317 (2010)

The metal-free combination of catalytic amounts of PPh3, B(C6F5)3, and PhSiH3 can efficiently hydrosilylate aldehydes, ketones, aldimines and ketimines to afford the corresponding reduction products in good yields.

Promotion of Sn on the Pd/AC catalyst for the selective hydrogenation of cinnamaldehyde

Zhao, Jia,Xu, Xiaoliang,Li, Xiaonian,Wang, Jianguo

, p. 102 - 106 (2014)

The effect of Sn on the Pd/AC catalysts for the selective hydrogenation of cinnamaldehyde (CALD) was investigated. TEM, EDX, XRD and XPS have been employed to characterize Pd-Sn/AC. 80% cinnamyl alcohol (COL) selectivity can be obtained at 96% CALD conversion, even 100% selectivity can be achieved at 3% conversion. The PdSn type alloy is responsible for the enhancement of unsaturated alcohol (UA) selectivity, as confirmed by XRD and EDX. XPS technique confirmed that the promoting effect of Sn was related to Pd-Sn interaction. The favorable adsorption of C = O bond on the PdSn has been supported by means of density functional theory.

Mild reduction of carboxylic acids to alcohols using cyanuric chloride and sodium borohydride

Falorni, Massimo,Porcheddu, Andrea,Taddei, Maurizio

, p. 4395 - 4396 (1999)

Several carboxylic acids, including N-Boc, N-Cbz and N-Fmoc amino acids were reduced to the corresponding alcohols by activation of the carboxy function with cyanuric chloride and N-methylmorpholine followed by reduction with aqueous sodium borohydride.

Cationic [2,6-Bis(2′-oxazolinyl)phenyl]palladium(II) Complexes: Catalysts for the Asymmetric Michael Reaction

Stark, Mark A.,Jones, Geraint,Richards, Christopher J.

, p. 1282 - 1291 (2000)

Reaction of 1,3-dicyanobenzene with β-amino alcohols (S)-H2NCHRCH2OH (R = iPr, iBu, tBu, CH2Cy, CH2Ph) and (R)-H2NCHPhCH2OH gave new 1,3-bis(2′-oxazolinyl)benzenes (30-51%). These, together with 1,3-bis(4′,4′-dimethyl-2′-oxazolinyl)benzene, were treated with LDA/TMEDA followed by the addition of PdBr2(1,5-COD) to give [2,6-bis(2′-oxazolinyl)phenyl]-palladium(II) bromide complexes (21-41%). In two cases no complexes were obtained (R = Ph, CH2Ph) due to ring opening of the oxazolines by LDA/TMEDA. Treatment of the palladium complexes with AgBF4, AgOTf, or AgSbF6 in wet CH2Cl2 provided a series of cationic [2,6-bis(2′-oxazolinyl)phenyl]palladium complexes (28-87%) containing water coordinated to palladium, as established by an X-ray crystal structure analysis of (S,S)-[2,6-bis(4′-isopropyl-2′-oxazolinyl)phenyl]aquopalladium(II) trifluoromethanesulfonate. All of the cationic complexes proved to be efficient catalysts for the Michael reaction between α-cyanocarboxylates and methyl vinyl ketone and between acrylonitrile and activated Michael donors. Selectivities of up to 34% ee were obtained for the formation of (R)-ethyl 2-cyano-2-methyl-5-oxohexanoate.

Photodeoxygenation of dibenzothiophene sulfoxide: Evidence for a unimolecular S-O cleavage mechanism

Gregory, Daniel D.,Wan, Zehong,Jenks, William S.

, p. 94 - 102 (1997)

Photolysis of dibenzothiophene sulfoxide results in the formation of dibenzothiophene and oxidized solvent. Though quantum yields are low, chemical yields of the sulfide are quite high. Yields of the oxidized solvents can also be high. Typical products are phenol from benzene, cyclohexanol, and cyclohexene from cyclohexane and 2-cyclohexenol and epoxycyclohexane from cyclohexene. A number of experiments designed to elucidate the mechanism of the hydroxylation were carried out, including measurements of quantum yields as a function of concentration, solvent, quenchers, and excitation wavelength. These data are inconsistent with a mechanism involving a sulfoxide dimer, which also does not properly account for the solvent oxidations. It is suggested hbat the active oxidizing agent may be atomic oxygen O(3P) or a closely related noncovalent complex, based on the nature of the oxidation chemistry, comparison to known rate constants for O(3P) reactivity, and the quantum yield data.

Pyridine: N-oxide promoted hydrosilylation of carbonyl compounds catalyzed by [PSiP]-pincer iron hydrides

Chang, Guoliang,Fenske, Dieter,Fuhr, Olaf,Li, Xiaoyan,Sun, Hongjian,Xie, Shangqing,Yang, Wenjing,Zhang, Peng

, p. 9349 - 9354 (2020)

Five [PSiP]-pincer iron hydrides 1-5, [(2-Ph2PC6H4)2HSiFe(H)(PMe3)2 (1), (2-Ph2PC6H4)2MeSiFe(H)(PMe3)2 (2), (2-Ph2PC6H4)2PhSiFe(H)(PMe3)2 (3), (2-(iPr)2PC6H4)2HSiFe(H)(PMe3) (4), and (2-(iPr)2PC6H4)2MeSiFe(H)(PMe3)2 (5)], were used as catalysts to study the effects of pyridine N-oxide and the electronic properties of [PSiP]-ligands on the catalytic hydrosilylation of carbonyl compounds. It was proved for the first time that this catalytic process could be promoted with pyridine N-oxide as the initiator at 30 °C because the addition of pyridine N-oxide is beneficial for the formation of an unsaturated hydrido iron complex, which is the key intermediate in the catalytic mechanism. Complex 4 as the best catalyst shows excellent catalytic performance. Among the five complexes, complex 3 was new and the molecular structure of complex 3 was determined by single crystal X-ray diffraction. A proposed mechanism was discussed.

Selective Reductions: 33. Potassium Triisopropoxyborohydride as a Selective Reducing Agent in Organic Synthesis. Reaction with Selected Organic Compounds Containing Representative Functional Groups

Brown, Herbert C.,Cha, Jin Soon,Nazer, Behrooz,Kim, Suk-Choong,Krishnamurthy, Sundaram

, p. 885 - 892 (1984)

The approximate rate and stoichiometry of the reaction of excess pure potassium triisopropoxyborohydride, KIPBH, with 56 selected compounds containing representative functional groups under standardized conditions (tetrahydrofuran, 0 deg C) was examined in order to define the characteristics of the reagent for selective reductions.Primary, secondary, and tertiary alcohols evolve hydrogen partially, even after a long period of time.Phenol also generates partial hydrogen, and the reactions of those amines and thiols studied with the reagent are very slow.Aldehydes andketones are reduced rapidly and quantitatively to give the corresponding alcohols.Unlike sodium and potassium borohydrides, KIPBH is very stereoselective. 2-Methylcyclohexanone can be reduced to the correspondingly less stable isomer, cis-2-methylcyclohexanol, in a high ratio (91percent cis isomer).Cinnamaldehyde is rapidly reduced to cinnamylalcohol, and further reduction is very slow under these conditions.Anthraquinone is cleanly reduced to 9,10-dihydro-9,10-anthracenediol.Carboxylic acids liberate hydrogen only partially, and further reduction is very slow.Acid chlorides consume 1 equiv of hydride rapidly, but the corresponding aldehydes do not form.Esters are almost inert toward the reagent. γ-Butyrolactone and phthalide are reduced only slowly.Epoxides are inert toward the reagent.Primary aliphatic amides evolve hydrogen slowly and primary aromatic amides evolve 1 equiv of hydrogen, but no significant reduction occurs.Tertiary amides and nitriles are inert toward the reagent.Of the nitrogen compounds studied, nitrobenzene is partially reduced after 48h, while azobenzene and azoxybenzene are inert.Partial reduction ofcyclohexanone oxime is observed, while phenyl isocyanate, pyridine, and pyridine N-oxide are inert under these conditions.Di n-butyl disulfide and diphenyl disulfide are reduced rapidly and quantitatively to the corresponding mercaptans with partial hydrogen evolution.Other sulfur compounds studied, such as p-tolyl methyl sulfide, diphenylsulfone, methanesulfonic acid, and p-toluenesulfonic acid, are inert toward the reagent.Only partial reduction of cyclohexyl tosylate is observed.Potassium triisopropoxyborohydride is a valuable reagent in boron chemistry.Thus, it transfers 1 equiv of hydride to dialkylhaloboranes, and the resulting dialkylborane can be transformed to a mixed trialkylborane, providing a potential route to mixed trialkylcarbinols or unsymmetrical ketones.The reagent rapidly transfers hydride to even severely hindered trialkylboranes, providing a simple synthetic route to these useful reagents.Finally, it readily converts 2-bromo-trans-vinylboronic esters to the cis-vinylboronic esters, providing a convenient synthetic route to these derivatives.

Hydrogenation of α,β-Unsaturated Aldehydes and Ketones to the Unsaturated Alcohols catalysed by Hydridoiridium Phosphine Complexes

Farnetti, E.,Pesce, M.,Kaspar, J.,Spogliarich, R.,Graziani, M.

, p. 746 - 747 (1986)

Unusual selective hydrogenation of cinnamaldehyde and benzylideneacetone to the corresponding unsaturated alcohols is catalysed by (+) complexes in toluene; use of a chiral phosphine gives a 7.4percent enantiomeric excess of (S)-(-)-1-phenylbut-1-en-3-ol.

Phosphine- and ammonium-functionalized ordered mesoporous carbons as supports for cluster-derived metal nanoparticles

Vidick,Leonard,Poleunis,Delcorte,Devillers,Hermans

, p. 112 - 126 (2014)

An ordered mesoporous carbon (OMC) was functionalized with ammonium or chelating phosphine ligands. In both cases, the functionalization procedure started by oxidation by nitric acid treatment, followed by activation of surface carboxylic acid groups with

Iron-Catalyzed Allylic Amination Directly from Allylic Alcohols

Emayavaramban, Balakumar,Roy, Moumita,Sundararaju, Basker

, p. 3952 - 3955 (2016)

Allylic amination, directly from alcohols, has been demonstrated without any Lewis acid activators using an efficient and regiospecific molecular iron catalyst. Various amines and alcohols were employed and the reaction proceeded through the oxidation/reduction (redox) pathway. A direct one-step synthesis of common drugs, such as cinnarizine and nafetifine, was exhibited from cinnamyl alcohol that produced water as side product. The iron way! A direct amination of allylic alcohols has been demonstrated without the need of Lewis acid activators using an efficient and regiospecific molecular iron catalyst. A range of amines and alcohols were tolerated, and the reaction was found to procced through an oxidation/reduction (redox) pathway (see scheme).

Simple and efficient 1,3-isomerization of allylic alcohols using a supported monomeric vanadium-oxide catalyst

Mitsudome, Takato,Sueoka, Shoichiro,Ikeda, Satoshi,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi

, p. 2879 - 2882 (2013)

Promotion by group high five: Silica-supported monomeric vanadium-oxide promoted the isomerization of various allylic alcohols, including under scaled-up and solvent-free reaction conditions. This catalyst also exhibited high reusability with no drop in activity.

Polymer Supported Zirconium Borohydride: a Stable, Efficient and Regenerable Reducing Agent

Tamami, Bahman,Goudarzian, Nouredin

, p. 1079 - 1080 (1994)

The unstable zirconium borohydride, Zr(BH4)4, is stabilized on polyvinylpyridine and used as a new, stable, efficient and regenerable polymer supported transition-metal borohydride reagent for reduction of a variety of carbonyl compounds.

Microwave assisted solid reaction: Reduction of esters to alcohols by potassium borohydride-lithium chloride

Feng,Liu,Dai,Yang,Tu

, p. 1875 - 1877 (2001)

Esters can be successfully reduced to the corresponding alcohols with potassium borohydride/lithium chloride under microwave irradiation without solvent. The reactions are generally completed in 2-8 minutes, with the yields varying from 55% to 95%.

Chemoselective transfer hydrogenation of carbonyl compounds catalyzed by macrocyclic nickel (II)complex

Phukan, Prodeep,Sudalai

, p. 2401 - 2405 (2000)

Macrocyclic Ni(II) complex, 1, catalyzes efficiently the chemoselective transfer reduction of carbonyl compounds in presence of propan-2-ol/KOH or HCO2H/HCO2NH4 as hydrogen donors to produce the corresponding alcohols in high yield.

-

Hutchins,R.O.,Kandasamy,D.

, p. 2530 - 2533 (1975)

-

Hydrosilylation of aldehydes and ketones catalyzed by an n-heterocyclic carbene-nickel hydride complex under mild onditions

Bheeter, Linus P.,Henrion, Mickael,Brelot, Lydia,Darcel, Christophe,Chetcuti, Michael J.,Sortais, Jean-Baptiste,Ritleng, Vincent

, p. 2619 - 2624 (2012)

Half-sandwich N-heterocyclic carbene (NHC)-nickel complexes of the general formula [NiACHTUNGTRENUNG(NHC)ClCp?] (Cp?= Cp, Cp*) efficiently catalyze the hydrosilylation of aldehydes and ketones at room temperature in the presence of a catalytic amount of sodium triethylborohydride and thus join the fairly exclusive club of well-defined nickel(II) catalyst precursors for the hydrosilylation of carbonyl functionalities. Of notable interest is the isolation of an intermediate nickel hydride complex that proved to be the real catalyst precursor.

Poly(n-butyl-4-vinylpyridinium) borohydride as a new stable and efficient reducing agent in organic synthesis

Khaligh, Nader Ghaffari,Ghasem-Abadi, Parisa Ghods,Mihankhah, Taraneh

, p. 23 - 29 (2014)

Sodium borohydride is stabilized on poly(n-butyl-4-vinylpyridinium) chloride, and it is used as an efficient and regenerable polymer-supported borohydride reagent for the reduction of a variety of carbonyl compounds, such as aldehydes, ketones, α,β-unsaturated carbonyl compounds, α-diketones, and acyloins.

A mild and chemoselective method for the deprotection of tert-butyldimethylsilyl (TBDMS) ethers using iron(III) tosylate as a catalyst

Bothwell, Jason M.,Angeles, Veronica V.,Carolan, James P.,Olson, Margaret E.,Mohan, Ram S.

, p. 1056 - 1058 (2010)

The most common method for the deprotection of TBDMS ethers utilizes stoichiometric amounts of tetrabutylammonium fluoride, n-Bu4N+F- (TBAF), which is highly corrosive and toxic. We have developed a mild and chemoselective method for the deprotection of TBDMS, TES, and TIPS ethers using iron(III) tosylate as a catalyst. Phenolic TBDMS ethers, TBDPS ethers and the BOC group are not affected under these conditions. Iron(III) tosylate is an inexpensive, commercially available, and non-corrosive reagent.

Regulating Hydrogenation Chemoselectivity of α,β-Unsaturated Aldehydes by Combination of Transfer and Catalytic Hydrogenation

Zhou, Yangyang,Li, Zihao,Liu, Yanbo,Huo, Jia,Chen, Chen,Li, Qiling,Niu, Songyang,Wang, Shuangyin

, p. 1746 - 1750 (2020)

Two hydrogenation mechanisms, transfer and catalytic hydrogenation, were combined to achieve higher regulation of hydrogenation chemoselectivity of cinnamyl aldehydes. Transfer hydrogenation with ammonia borane exclusively reduced C=O bonds to get cinnamyl alcohol, and Pt-loaded metal–organic layers efficiently hydrogenated C=C bonds to synthesize phenyl propanol with almost 100 % conversion rate. The hydrogenation could be performed under mild conditions without external high-pressure hydrogen and was applicable to various α,β-unsaturated aldehydes.

SELECTIVE REDUCTION OF ALDEHYDES BY A FORMIC ACID- TRIALKYLAMINE- RuCl2(PPh3)3 SYSTEM

Khai, Bui The,Arcelli, Antonio

, p. 3365 - 3368 (1985)

In the presence of trialkylamine and formic acid, RuCl2(PPh3)3 selectively reduces aldehydes to the corresponding alkohols at room temperature.Other reducible groups are unaffected.

Facile and chemoselective reduction of carboxylic acids into alcohols via sodium borohydride reduction of N-acylbenzotriazoles

Singh, Kamal Nain,Kaur, Amarjit

, p. 2935 - 2937 (2005)

Carboxylic acids are converted into corresponding alcohols by chemoselective reduction of their benzotriazole amides with sodium borohydride. Copyright Taylor & Francis, Inc.

A mild method for the deprotection of tetrahydropyranyl (THP) ethers catalyzed by iron(III) tosylate

Bockman, Matthew R.,Angeles, Veronica V.,Martino, Julia M.,Vagadia, Purav P.,Mohan, Ram S.

, p. 6939 - 6941 (2011)

A mild method for the deprotection of THP ethers catalyzed by iron(III) tosylate (2.0 mol %) in CH3OH has been developed. Iron(III) tosylate, Fe(OTs)3·6H2O, is a commercially available solid that is inexpensive, noncorrosive, and easy to handle. The room temperature reaction conditions make this method attractive for deprotection of a range of THP ethers.

Enhanced Reducing Properties of Pyridine-Borane Adsorbed on Solid Supports: A Convenient Method for Chemoselective Reduction of Aldehydes

Babler, James H.,Sarussi, Steven J.

, p. 4416 - 4419 (1983)

-

Caro's acid supported on silica gel. Part V: A mild and selective reagent for conversion of trimethyl silyl ethers to the corresponding hydroxy compounds

Lakouraj,Tajbakhsh,Khojasteh

, p. 1865 - 1870 (2003)

Mild and efficient method for deprotection of silyl ethers to alcohols is described using Caro's acid supported on silica gel. Reactions are carried out in dichloromethane at room temperature and their parent hydroxy compounds obtained in good to excellent yields. Using this procedure, tetrahydropyranyl ethers (THP) remain intact during desilylation reaction.

BOROHYDRIDE REDUCING AGENT DERIVED FROM ANION EXCHANGE RESIN : SELECTIVE REDUCTION OF α, β-UNSATURATED CARBONYL COMPOUNDS.

Sande, A. R.,Jagadale, M. H.,Mane, R. B.,Salunkhe, M. M.

, p. 3501 - 3504 (1984)

Borohydride exchange resin (BER) exhibited selectivity in the reduction of α, β-unsaturated carbonyl compounds to the corresponding unsaturated alcohols.

New heterogeneous B(OEt)3-MCM-41 catalyst for preparation of α,β-unsaturated alcohols

Uysal, Burcu,Oksal, Birsen S.

, p. 3893 - 3911 (2013)

Grafting of boron tri-ethoxide on mesoporous MCM-41 resulted in a highly active catalyst for the Meerwein-Ponndorf-Verley (MPV) reduction and the catalyst denoted as B(OEt)3-MCM-41. Chemoselective reduction of α,β-unsaturated aldehydes and ketones to the corresponding α,β-unsaturated alcohols was achieved by MPV reduction reaction using a new B(OEt)3-MCM-41 catalyst. The prepared new heterogeneous catalyst, B(OEt)3-MCM-41, was characterized in detail by using XRD, 29Si NMR-, 11B NMR-, 13C NMR-, and TEM, N2 adsorption, and ICP-OES. The results demonstrated the successful homogenous distribution of the B(OEt)3 on the MCM-41 support. The heterogeneous B(OEt)3-MCM-41 catalyst, in comparison with the homogeneous B(O i Pr)3 and B(OEt)3 catalysts, displayed similiar catalytic activity in the MPV reduction of α,β-unsaturated aldehydes and ketones with alcohols as reductants. Reduced reaction times and very high selectivities for the unsaturated alcohols were obtained with the heterogenous catalyst compared with the homogeneous catalysts. The B(OEt)3-MCM-41 catalyst was found to be encouraging, as is is recyclable up to six cycles without any significant loss in its catalytic activity.

Tuning Cu Overvoltage for a Copper-Telluride System in Electrocatalytic Water Reduction and Feasible Feedstock Conversion: A New Approach

Johny, Jinta Merlin,Karthick, Kannimuthu,Kumaravel, Sangeetha,Kundu, Subrata,Sankar, Selvasundarasekar Sam,Thiruvengetam, Prabaharan

, (2020)

Highly efficient and earth-abundant elements capable of water reduction by electrocatalysis and are attractive for the sustainable generation of fuels. Among the earth-abundant metals, copper is one of the cheapest but often the most neglected choice for the hydrogen evolution reaction (HER) due to its high overvoltage. Herein, for the first time we have tuned the overpotential of copper by tellurizing it by two different methodologies, viz. hydrothermal and wet chemical methods, which form copper telluride nanochains and aggregates. The application of copper telluride as an electrocatalyst for the HER gave fruitful results in terms of both activity and stability. The hydrothermally synthesized catalyst Cu2-xTe/hyd shows a low overpotential (347 mV) at 10 mA cm-2 toward the HER. In addition, the catalyst showed a very low charge transfer resistance (Rct) of 24.4 ω and, as expected, Cu2-xTe/hyd exhibited a lower Tafel slope value of 188 mV/dec in comparison to Cu2-xTe/wet (280 mV/dec). A chronoamperometry study reveals the long-term stability of both catalysts even up to 12 h. The Faradaic efficiency of Cu2-xTe/hyd was calculated and found to be 95.06percent by using gas chromatographic (GC) studies. Moreover, with the idea of utilizing produced hydrogen (H2) from electrocatalysis, for the first time we have carried out feedstock conversion to platform chemicals in water under eco-friendly green conditions. We have chosen cinnamaldehyde, 2-hydroxy-1-phenylethanone, 4-(benzyloxy)benzaldehyde, and 2-(3-methoxyphenoxy)-1-phenylethanone (β-O-4) as model compounds for feedstock conversion by hydrogenation and/or hydrogenolysis reactions in aqueous medium using external hydrogen pressure. This protocol could also be scaled up for large-scale conversion and the catalyst is likely to find industrial application since it requires an inexpensive catalyst and an easily available, mild reducing agent. The robustness of the developed catalyst is proven by recyclability experiments and its possibility of use in real-life applications.

-

Rylander,Steele

, p. 1579 (1969)

-

Selective Deprotection of the Diphenylmethylsilyl (DPMS) Hydroxyl Protecting Group under Environmentally Responsible, Aqueous Conditions

Akporji, Nnamdi,Lieberman, Josh,Maser, Michael,Yoshimura, Masahiko,Boskovic, Zarko,Lipshutz, Bruce H.

, p. 5743 - 5747 (2019)

Two new methods for selective deprotection of diphenylmethylsilyl (DPMS) ethers are described. Unmasking can be achieved with either catalytic amounts of perfluoro-1-butanesulfonyl fluoride (a SuFEx reagent) under mild, aqueous micellar conditions, or using stoichiometric amounts of 18-crown-6 ether in aqueous ethanol.

Chemoselective reduction of carbonyl compounds to alcohols with co-doped ammonia borane

Huang, Pengmian,Tang, Wenjuan,Tan, Guishan,Zeng, Wenbin,Li, Yuanjian,Zhang, Qinghua,Chen

, p. 8248 - 8250 (2014)

Chemoselective reduction of various carbonyl compounds to alcohols with Co-doped ammonia borane was investigated in the present work. It was observed that Co-doped ammonia borane exhibited much better performance than ammonia borane. The Co-based catalysts could be reused up to four times with a slight decrease in activity. Thus, a mild and efficient method for chemoselective reduction of carbonyl compounds with Co-doped ammonia borane was established. The Co-doped ammonia borane sample was characterized by electron paramagnetic resonance. Electron paramagnetic resonance characterization revealed that Co element in a partially reduced state.

Reduction of carbonylic and carboxylic groups by plant cell cultures

Villa, Raffaella,Molinari, Francesco

, p. 693 - 696 (2008)

The transformation of aliphatic and aromatic acids to their corresponding alcohols, involving two reductive steps, is difficult to perform biologically due to its low redox potential. For this reason, the reduction of nonactivated carboxylic acids has been described for only a limited number of substrates and confined to a few microbial groups (fungi, clostridia, and archea). Nine species of cultured plant cells were able to reduce cinnamic, hexanoic, and octanoic acids to the corresponding primary alcohols with yields ranging from 2 to 80% (w/w). Aldehyde was detected only for three species during the reduction of cinnamic acid, confirming that the second reductive step from aldehyde to alcohol is faster than the first, from acid to aldehyde. Lyophilized cells from some of the cultures were used in buffer and solvent-water systems to obtain the reduction of carbonylic (ethyl acetoacetate) and carboxylic (cinnamic and hexanoic acids) groups.

Low-temperature reduction of bio-based cinnamaldehyde to α,β-(un)saturated alcohols enabled by a waste-derived catalyst

Jian, Yumei,Li, Hu,Luo, Xiaoxiang

, (2022/01/06)

A waste eggshell-derived catalyst (CaO-900) was facilely prepared and exhibited high efficiency in selective hydrogenation of bio-based cinnamaldehyde (CAL) to cinnamyl alcohol (COL) with 97% yield at 30 °C. By simply adjusting reaction temperature and time, CAL could be completely converted to 3-phenylpropanol. The predominant catalytic performance of CaO-900 could be attributed to its high alkalinity and large specific surface area. In situ Raman and theoretical calculations indicated that the priority of hydrosilylation toward CAL played a crucial role in the control of product distribution. In addition, the CaO-900 catalyst showed good recyclability.

Synthesis of aluminum doped MIL-100(Fe) compounds for the one-pot photocatalytic conversion of cinnamaldehyde and benzyl alcohol to the corresponding alcohol and aldehyde under anaerobic conditions

Guo, Binbin,Kang, Yueyue,Shi, Yingzhang,Wang, Zhiwen,Wu, Ling

, p. 184 - 192 (2022/02/03)

Fully utilizing the photogenerated electrons and holes in a photocatalytic process is a promising way to enhance catalytic efficiency and achieve atomic economy. Here, conjugated photocatalytic redox reactions, i.e. hydrogenation of cinnamaldehyde (CAL) t

Silver-Catalyzed Hydroboration of C-X (X = C, O, N) Multiple Bonds

Pandey, Vipin K.,Tiwari, Chandra Shekhar,Rit, Arnab

supporting information, p. 1681 - 1686 (2021/03/03)

AgSbF6 was developed as an effective catalyst for the hydroboration of various unsaturated functionalities (nitriles, alkenes, and aldehydes). This atom-economic chemoselective protocol works effectively under low catalyst loading, base- A nd solvent-free moderate conditions. Importantly, this process shows excellent functional group tolerance and compatibility with structurally and electronically diverse substrates (>50 examples). Mechanistic investigations revealed that the reaction proceeds via a radical pathway. Further, the obtained N,N-diborylamines were showcased to be useful precursors for amide synthesis.

PNO ligand containing planar chiral ferrocene and application thereof

-

Paragraph 0114-0118, (2021/06/21)

The invention discloses a PNO ligand containing planar chiral ferrocene and application thereof. The PNO ligand containing planar chiral ferrocene is a planar chiral ferrocene-containing and phenol-containing PNO ligand as shown in a general formula (I) or (II) which is described in the specification, or a planar chiral ferrocene-containing and aryl-phosphoric-acid-containingPNO ligand containing as shown in a general formula (III) or (IV) which is described in the specification, or a planar chiral ferrocene-containing and carbon-chiral-phenol-containingPNO ligand as shown in a general formula (V) or (VI) which is described in the specification. The invention provides tridentate PNO ligands and processes for their complexation with transition metal salts or transition metal complexes; the introduction of salicylaldehyde and derivatives thereof, which are simple and easy to obtain, enables the ligands to have a bifunctionalization effect, and -OH in a formed catalyst has stronger acidity and is beneficial to combination with N/O in polar double bonds. Therefore, due to the bifunctionalization effect of the catalyst, the interaction between the catalyst and a substrate can be greatly improved, so a reaction can obtain higher catalytic activity and stereoselectivity.

Platinum supported on nanosilica and fibrous nanosilica for hydrogenation reactions

Erasmus, E.,Xantini, Z.

, (2020/11/24)

Platinum nanoparticles supported on nanosilica (NP) and fibrous nanosilica (dendritic fibrous nano-spheres, DFNS) were prepared by direct grafting of the Pt precursor onto the silanol groups or via a polyethylenimine (PEI) linker. From the SEM and TEM images the average diameter of the nanosilica and fibrous nanosilica (DFNS), was determined to be 21.4 and 503 nm, respectively. While surface areas as measured by ASAP is 463.4 m2 g?1 for DFNS and 142.5 m2 g?1 for the nanosilica. For the four Pt containing catalysts (Pt/NP, Pt/DFNS, Pt/PEI/NP and Pt/PEI/DFNS), a Pt loading between 1.35 × 1017 and 8.46 × 1017 Pt atoms per gram support were determined. The PEI-containing catalyst gave higher Pt-loading than the direct anchoring of the Pt onto the silanol groups of the support. The catalysts were further characterised ATR FTIR and XPS. After oxidation of the pre-catalysts 85% of the Pt was in the oxide form. While after reduction, ca. 82% the Pt supported on DFNS was in the metallic form. Reduction of the Pt supported on NP, resulted in 100% of the Pt in the Pt0 oxidation state. These catalysts were tested for the hydrogenation of C[dbnd]C and/or C[dbnd]O bonds in cyclohexene, benzaldehyde and cinnamaldehyde. The % conversion and product distribution will be discussed in term of diameter, surface area and Pt-loading.

Process route upstream and downstream products

Process route

3-phenyl-propenal
104-55-2

3-phenyl-propenal

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

ethylbenzene
100-41-4,27536-89-6

ethylbenzene

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
Conditions Yield
With hydrogen; at 90 ℃; under 3750.38 Torr;
Conditions
Conditions Yield
With oxygen; isobutyraldehyde; In acetonitrile; at 60 ℃; for 3h; under 760.051 Torr; Reflux; Autoclave;
3-phenyl-propenal
104-55-2

3-phenyl-propenal

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

3-Phenylpropenol
104-54-1

3-Phenylpropenol

2-phenylethanol
60-12-8

2-phenylethanol

formic acid phenethyl ester
104-62-1

formic acid phenethyl ester

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With D-glucose; Baeyer?Villiger monooxygenase from Aspergillus oryzyae; ene reductase from Saccharomyces cerevisiae S288C; glycerol; In aq. buffer; at 25 ℃; for 24h; pH=8; Enzymatic reaction;
3-phenyl-propenal
104-55-2

3-phenyl-propenal

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

3-Phenylpropenol
104-54-1

3-Phenylpropenol

2-phenylethanol
60-12-8

2-phenylethanol

benzyl formate
104-57-4

benzyl formate

formic acid phenethyl ester
104-62-1

formic acid phenethyl ester

phenylacetaldehyde
122-78-1

phenylacetaldehyde

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With D-glucose; Baeyer?Villiger monooxygenase from Aspergillus oryzyae; ene reductase from Saccharomyces cerevisiae S288C; glycerol; In aq. buffer; at 25 ℃; for 2h; pH=8; Enzymatic reaction;
allylbenzene
300-57-2,57807-91-7

allylbenzene

3-Phenylpropenol
104-54-1

3-Phenylpropenol

benzaldehyde
100-52-7

benzaldehyde

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
Conditions Yield
With tert.-butylhydroperoxide; dirhodium tetraacetate; In acetic acid; at 25 ℃; for 72h; Product distribution;
1.33 mmol
0.79 mmol
0.36 mmol
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

methyl magnesium iodide
917-64-6

methyl magnesium iodide

diethyl ether
60-29-7,927820-24-4

diethyl ether

3-Phenylpropenol
104-54-1

3-Phenylpropenol

3-(2-methylphenyl)prop-2-en-1-al
93614-78-9,4549-82-0

3-(2-methylphenyl)prop-2-en-1-al

Conditions
Conditions Yield
diethyl ether
60-29-7,927820-24-4

diethyl ether

methyl magnesium <sup>(1+)</sup>; bromide

methyl magnesium (1+); bromide

3-phenyl-propenal
104-55-2

3-phenyl-propenal

3-Phenylpropenol
104-54-1

3-Phenylpropenol

3-(2-methylphenyl)prop-2-en-1-al
93614-78-9,4549-82-0

3-(2-methylphenyl)prop-2-en-1-al

Conditions
Conditions Yield
ethanol
64-17-5

ethanol

EtOMgCl

EtOMgCl

benzaldehyde
100-52-7

benzaldehyde

3-Phenylpropenol
104-54-1

3-Phenylpropenol

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
ethanol
64-17-5

ethanol

EtOMgCl

EtOMgCl

benzaldehyde
100-52-7

benzaldehyde

3-Phenylpropenol
104-54-1

3-Phenylpropenol

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
3-phenyl-propenal
104-55-2

3-phenyl-propenal

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

3-Phenylpropenol
104-54-1

3-Phenylpropenol

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
unter vermindertem Druck;

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