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Cas Database

100-06-1

100-06-1

Identification

Synonyms:Acetophenone,4'-methoxy- (8CI);Benzophenone, p-methoxy- (3CI);1-(4-Methoxyphenyl)ethanone;1-Acetyl-4-methoxybenzene;4-Acetylanisole;4-Methoxyphenyl methyl ketone;Acetoanisole;Linarodin;Methyl 4-methoxyphenyl ketone;Methyl p-methoxyphenyl ketone;Novatone;Vananote;p-Acetylanisole;p-Anisyl methyl ketone;p-Methoxy(acetyl)benzene;p-Methoxyacetophenone;p-Methoxyphenyl methyl ketone;para-Methoxyacetophenone;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowed

  • 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. /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aromatic hydrocarbons and related compounds/

  • Fire-fighting measures: Suitable extinguishing media 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. ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. 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. Keep container tightly closed in a dry and well-ventilated place. Light sensitive. Storage class (TRGS /technical rules for hazardous substances/ 510): Non Combustible Solids.

  • 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

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:4''-Methoxyacetophenone
  • Packaging:5g
  • Price:$ 55
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4'-Methoxyacetophenone >99.0%(GC)
  • Packaging:25g
  • Price:$ 24
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4'-Methoxyacetophenone >99.0%(GC)
  • Packaging:500g
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4'-Methoxyacetophenone 99%
  • Packaging:250 g
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4'-Methoxyacetophenone 99%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acetanisole ≥98%, FCC, FG
  • Packaging:5 kg
  • Price:$ 390
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acetanisole ≥98%, FCC, FG
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acetanisole ≥98%, FCC, FG
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acetanisole ≥98%, FCC, FG
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  • Price:$ 116
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4′-Methoxyacetophenone 99%
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Relevant articles and documentsAll total 1087 Articles be found

Regeneration of carbonyl compounds by oxidative cleavage of oximes with NBS in the presence of β-cyclodextrin in water

Reddy, M. Somi,Narender,Rao, K. Rama

, p. 3875 - 3881 (2004)

The conversion of different oximes to the corresponding carbonyl compounds was carried out at room temperature in good to high yields with N-bromosuccinimide in water in the presence of β-cyclodextrin.

-

Alper et al.

, p. 2861 (1977)

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First example of water-soluble transition-metal catalysts for Oppenauer-type oxidation of secondary alcohols

Ajjou, Abdelaziz Nait

, p. 13 - 16 (2001)

The first water-soluble transition-metal catalysts for Oppenauer-type oxidation of secondary alcohols have been developed. The catalytic system composed of [Ir(COD)Cl]2, 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt (BQC) and sodium carbonate is highly efficient for the selective oxidation of benzylic and aliphatic secondary alcohols to the corresponding ketones with catalyst/substrate ratios ranging from 0.4 to 2.5 percent. The substitution of [Ir(COD)Cl]2 by its rhodium analog [Rh(COD)Cl]2 generates a less active catalytic system. [Ir(COD)Cl]2/BQC was also found to be more active than its water-insoluble analog system [Ir(COD)Cl]2/2,2'-biquinoline (BC).

Nickel boride mediated cleavage of 1,3-oxathiolanes: A convenient approach to deprotection and reduction

Khurana, Jitender M.,Magoo, Devanshi,Dawra, Kiran

, p. 1113 - 1116 (2016)

1,3-Oxathiolanes are rapidly cleaved by nickel boride allowing regeneration of corresponding carbonyl compounds. Optimum reaction conditions have also been defined to obtain alcohols exclusively by reduction of oxathiolanes. Reactions are rapid at room temperature and do not require protection from atmosphere. Mild reaction conditions, simple work up, and high yields are some of the major advantages of the procedure.

A Mild and Efficient Oxidation of Alcohols to Ketones with Iodosobenzene/(Salen) Manganese Complex

Kim, Sung Soo,Borisova, Galina

, p. 3961 - 3967 (2003)

An excellent method for the chemoselective oxidation of alcohols to ketones with C6H5IO catalyzed by (salen) manganese/4A MS in CH3CN has been devised. The reported procedure is fast, simple, and the yields are excellent (> 95%) in most cases.

An efficient and practical aerobic oxidation of benzylic methylenes by recyclable: N -hydroxyimide

Wang, Jian,Zhang, Cheng,Ye, Xiao-Qing,Du, Wenting,Zeng, Shenxin,Xu, Jian-Hong,Yin, Hong

, p. 3003 - 3011 (2021)

An efficient and practical benzylic aerobic oxidation catalyzed by cheap and simple N-hydroxyimide organocatalyst has been achieved with high yields and broad substrate scope. The organocatalyst used can be recycled and reused by simple workup and only minute amount (1 mol% in most cases) of simple iron salt is used as promoter. Phenyl substrates with mild and strong electron-withdrawing group could also be oxygenated in high yields as well as other benzylic methylenes. Influence of substituents, gram-scale application, catalysts decay and general mechanism of this methodology has also been discussed. This journal is

TEMPO-tert-butyl nitrite: An efficient catalytic system for aerobic oxidation of alcohols

He, Xijun,Shen, Zhenlu,Mo, Weimin,Sun, Nan,Hu, Baoxiang,Hu, Xinquan

, p. 89 - 92 (2009)

A metal-free catalytic system consisting of 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) and tert-butyl nitrite has been developed to activate molecular oxygen for the aerobic oxidation of alcohols. A variety of active and non-active alcohols were oxidized to their corresponding carbonyl compounds in high selectivity and yields.

Stereoselective oxidation and reduction by immobilized Geotrichum candidum in an organic solvent

Nakamura, Kaoru,Inoue, Yuko,Matsuda, Tomoko,Misawa, Ibuki

, p. 2397 - 2402 (1999)

Cells of the fungus, Geotrichwn candidum, were immobilized on a water-absorbing polymer and used for stereoselective oxidation and reduction in an organic solvent using cyclohexanone, cyclopentanol or alkan-2-ols as additive. Enantiomerically pure (.β)-1-arylethanols were obtained by the stereoselective oxidation of racemic 1-arylethanols, whereas enantiomerically pure (S)- 1-arylethanols were obtained by the reduction of the corresponding ketones, in contrast to reduction in water by the free cells in which (R)- or (S)- 1-arylethanols were produced in low ee. The reaction mechanism was investigated by measuring the partition of the substrates and products between the organic phase and aqueous phase in the polymer around which the cells were immobilized. Deuterated compounds were used to determine the role of the additives.

Enantiocomplementary C–H Bond Hydroxylation Combining Photo-Catalysis and Whole-Cell Biocatalysis in a One-Pot Cascade Process

Peng, Yongzhen,Li, Danyang,Fan, Jiajie,Xu, Weihua,Xu, Jian,Yu, Huilei,Lin, Xianfu,Wu, Qi

, p. 821 - 825 (2020)

Enantiocomplementary hydroxylation of alkyl aromatics through a one-pot photo-biocatalytic cascade reaction is described. The photoredox process is implemented in aqueous phase with O2 as oxidant and the subsequent (R)- or (S)-selective bioreduction is performed by whole cell system without the addition of the expensive cofactor (NADPH). This mild, operationally simple protocol transforms a wide variety of readily available aromatic compounds into valuable chiral alcohols with high yield (up to 90 %) and stereoselectivity (up to 99 %), thereby displaying important potentials in organic synthesis.

Selective oxidation of C–H bonds with Fe-N-C single-atom catalyst

Li, Xingwei

, p. 1 - 3 (2018)

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Catalytic Friedel-Crafts acylation of alkoxybenzenes mediated by aluminum hydrogensulfate in solution and solvent-free conditions

Salehi, Peyman,Khodaei, Mohammad Mehdi,Zolfigol, Mohammad Ali,Sirouszadeh, Sara

, p. 1863 - 1864 (2003)

Friedel-Crafts acylation of alkoxybenzenes was achieved efficiently by a reaction with aliphatic acid anhydrides in the presence of catalytic amounts of aluminum hydrogensulfate, Al(HSO4)3, in nitromethane and under solvent-free conditions. Alkylbenzenes and aryl halides, as well as aromatic anhydrides, remained intact under these conditions.

Liquid-phase oxidation of 1-isopropyl- and 1-ethyl-4-methoxybenzenes with oxygen to hydroperoxides

Zawadiak, Jan,Stec, Zbigniew,Jakubowski, Bartlomiej,Orlinska, Beata

, p. 89 - 94 (2003)

A study was carried out on the kinetics of free-radical chain oxidation of 1-isopropyl-4-methoxybenzene (1a) and 1-ethyl-4-methoxybenzene (1b) with oxygen in the liquid phase to yield 1-methyl-1-(4-methoxyphenyl)ethyl hydroperoxide (2a) and 1-(4-methoxyphenyl)ethyl hydroperoxide (2b). The oxidizability of 1a and 1b was studied over the temperature range 50-100°C. Long-term oxidations of 1a and 1b to the corresponding hydroperoxides were carried out and the properties and thermal stability of 2a were established.

A Novel Catalyst System, Antimony(V) Chloride-Lithium Perchlorate (SbCl5-LiClO4), in the Friedel-Crafts Acylation Reaction

Mukaiyama, Teruaki,Suzuki, Kaoru,Han, Jeong Sik,Kobayashi, Shu

, p. 435 - 438 (1992)

A novel catalyst system consisting of antimony(V) chloride (SbCl5) and lithium perchlorate (LiClO4) effectively promotes the Friedel-Crafts acylation reaction of aromatic compounds with acid anhydrides.

Efficient and recyclable rare earth-based catalysts for Friedel-Crafts acylations under microwave heating: Dendrimers show the way

Perrier, Arnaud,Keller, Michel,Caminade, Anne-Marie,Majoral, Jean-Pierre,Ouali, Armelle

, p. 2075 - 2080 (2013)

The catalytic system involving Sc(OTf)3 and a dendritic terpyridine ligand is able to promote the Friedel-Crafts acylation of a wide range of aromatics under microwave irradiation. The expected products are obtained in high yields after short reaction times and the nano-sized catalyst can be recovered and successfully used in 12 consecutive runs.

A supported manganese complex with amine-bis(phenol) ligand for catalytic benzylic C(sp3)-H bond oxidation

Karimpour, Touraj,Safaei, Elham,Karimi, Babak

, p. 14343 - 14351 (2019)

With regards to the importance of direct and selective activation of C-H bonds in oxidation processes, we develop a supported manganese amine bis(phenol) ligand complex as a novel catalyst with the aim of obtaining valuable products such as carboxylic acids and ketones that have an important role in life, industry and academic laboratories. We further analyzed and characterized the catalyst using the HRTEM, SEM, FTIR, TGA, VSM, XPS, XRD, AAS, and elemental analysis (CHN) techniques. Also, the catalytic evaluation of our system for direct oxidation of benzylic C-H bonds under solvent-free condition demonstrated that the heterogeneous form of our catalyst has high efficiency in comparison with homogeneous ones due to more stability of the supported complex. Furthermore, the structural and morphological stability of our efficient recyclable catalytic system has been investigated and all of the data proved that the complex was firmly anchored to the magnetite nanoparticles.

Palladium(II)-catalyzed desulfitative synthesis of aryl ketones from sodium arylsulfinates and nitriles: Scope, limitations, and mechanistic studies

Skillinghaug, Bobo,Sk?ld, Christian,Rydfjord, Jonas,Svensson, Fredrik,Behrends, Malte,S?vmarker, Jonas,Sj?berg, Per J. R.,Larhed, Mats

, p. 12018 - 12032 (2014)

A fast and efficient protocol for the palladium(II)-catalyzed production of aryl ketones from sodium arylsulfinates and various organic nitriles under controlled microwave irradiation has been developed. The wide scope of the reaction has been demonstrated by combining 14 sodium arylsulfinates and 21 nitriles to give 55 examples of aryl ketones. One additional example illustrated that, through the choice of the nitrile reactant, benzofurans are also accessible. The reaction mechanism was investigated by electrospray ionization mass spectrometry and DFT calculations. The desulfitative synthesis of aryl ketones from nitriles was also compared to the corresponding transformation starting from benzoic acids. Comparison of the energy profiles indicates that the free energy requirement for decarboxylation of 2,6-dimethoxybenzoic acid and especially benzoic acid is higher than the corresponding desulfitative process for generating the key aryl palladium intermediate. The palladium(II) intermediates detected by ESI-MS and the DFT calculations provide a detailed understanding of the catalytic cycle. (Figure Presented).

N- Hydroxyphthalimide and transition metal salts as catalysts of the liquid-phase oxidation of 1-methoxy-4-(1-methylethyl)benzene with oxygen

Orlinska, Beata,Romanowska, Iwona

, p. 670 - 676 (2011)

The oxidation process of 1-methoxy-4-(1-methylethyl)benzene catalysed by N-hydroxyphthalimide (NHPI) or NHPI in combination with Cu(II), Co(II), Mn(II) and Fe(II) salts was studied. The effects of the amount of catalyst and the temperature were determined

Clean and highly selective oxidation of alcohols in an ionic liquid by using an ion-supported hypervalent iodine(III) reagent

Qian, Weixing,Jin, Erlei,Bao, Weiliang,Zhang, Yongmin

, p. 952 - 955 (2005)

Alcohol consumption: The Phl(OAc)2-derived hypervalent iodine reagent 1 acts as an oxidant in the conversion of primary and secondary alcohols 2 into carbonyl compounds 3 with good to excellent yields (see scheme). The bromide ion remaining from the preparation of [emim]+[BF 4]-(emim = 1-ethyl-3-methylimidazolium tetrafluoroborate) acts as a catalyst in the reaction. Primary alcohols are oxidized without any detectable overoxidation.

Solid state cleavage of oximes with potassium permanganate supported on alumina

Imanzadeh,Hajipour,Mallakpour

, p. 735 - 740 (2003)

A manipulatively simple and rapid method for conversion of oximes to the corresponding carbonyl compounds is described. The reaction is conducted under solvent-less conditions using alumina-supported permanganate. According to the reaction system and conditions used, different ketones and aldehydes are obtained in moderate and good yields.

Metal Sulfonate Polymers as Catalysts for the Heterogeneous Acylation of Aromatic Derivatives

Morizur, Vincent,Hector, Daphné,Olivero, Sandra,Desmurs, Jean Roger,Du?ach, Elisabet

, p. 3126 - 3129 (2016)

A series of metal sulfonate salts attached to a poly(ether ether ketone) (PEEK) polymer were prepared by ultrasonic activation and then examined as heterogeneous catalysts in the Friedel–Crafts acylation of aromatic derivatives.

p-Methoxyphenacyl Esters as Photodeblockable Protecting Groups for Phosphates

Epstein, William W.,Garrossian, Massoud

, p. 532 - 533 (1987)

p-Methoxyphenacyl esters of substituted phosphates have been found to be photosensitive protecting groups which may be useful in biologically important phosphate synthesis.

Sur l'effet ipso du silicium lors de l'acylation du m-trimethylsilylanisole

Bennetau, B.,Krempp, M.,Dunogues, J.

, p. 263 - 268 (1987)

The acylation of m-trimethylsilylanisole which led to a significant amount of silylated acylanisoles was thoroughly investigated.This demonstrates with certainty that the ipso effect of the trimethylsilyl group generally admitted in this case is countered by the methoxy effect.

Reactions of silica chloride (SiO2Cl)/DMSO, a heterogeneous system for the facile regeneration of carbonyl compounds from thioacetals and ring-expansion annelation of cyclic thioacetals

Firouzabadi, Habib,Iranpoor, Nasser,Hazarkhani, Hassan,Karimi, Babak

, p. 2572 - 2576 (2002)

Silica chloride (SiO2Cl)/DMSO, as a heterogeneous system, has been efficiently used for deprotection of thioacetals into aldehydes in dry CH2Cl2 at room temperature. Thioketals without enolizable hydrogens adjacent to a sulfur atom are converted easily to the corresponding ketones in high yields under similar reaction conditions. However, thioketals with enolizable methyl and methylene groups undergo ring-expansion reactions to afford 1,4-dithiepins and 1,4-dithiins in dry CH2Cl2 at room temperature in good yields.

Sulfoximidations of Benzylic C?H bonds by Photocatalysis

Wang, Han,Zhang, Duo,Bolm, Carsten

, p. 5863 - 5866 (2018)

An efficient photocatalytic functionalization of compounds with benzylic C?H bonds by sulfoximidation in visible light is described. The mild reaction conditions allow the use of a broad array of substrates, including diarylmethane, alkyl arenes, arylacetonitrile, 2-arylacetate, and alkynyl aryl methanes. The sulfoximidation process is highly chemoselective and leads to the corresponding sulfoximines in generally good yields. Mechanistic investigations suggested the intermediacy of sulfoximidoyl radicals.

VO(acac)2 catalyzed oxidative deprotection of oximes, hydrazones, and semicarbazones

De, Surya Kanta

, p. 4409 - 4415 (2004)

Oximes, hydrazones, and semicarbazones undergo facile deprotection in the presence of a catalytic amount of vanadyl acetylacetonate and hydrogen peroxide in acetone at room temperature.

Acid-catalyzed hydration of alkynes in aqueous microemulsions

Nairoukh, Zackaria,Avnir, David,Blum, Jochanan

, p. 430 - 432 (2013)

Terminal aromatic alkynes are converted rapidly into ketones in a regioselective manner by treatment of their microemulsions with 0.33 M mineral acid between 80 and 140 °C. Internal and aliphatic acetylenes are likewise hydrated, but require longer reaction periods. The products are easily isolated from the reaction mixtures by phase separation. Replacement of H2O by D2O leads to the formation of trideuteriomethyl ketones. Copyright

Biphasic copper-catalyzed C–H bond activation of arylalkanes to ketones with tert-butyl hydroperoxide in water at room temperature

Hossain, Md. Munkir,Shyu, Shin-Guang

, p. 4252 - 4257 (2016)

A facile C–H bond activation of arylalkanes to their corresponding ketones catalyzed by copper salts using tert-butyl hydroperoxide as an oxidant in water at room temperature is described. Easy product separation, simple reaction procedures (without using base or phase transfer catalysis), and catalyst recycling make the catalytic system attractive. It is also active beyond activated benzylic methylene positions and could tolerate factionalized arylalkanes with diverse groups.

Oxidation of alcohols with molecular oxygen promoted by Nafion ionomer anchored pyrochlore composite at room temperature

Venkatesan,Kumar, A. Senthil,Zen

, p. 4339 - 4341 (2008)

Nafion ionomer anchored ruthenium oxide pyrochlore composite has been demonstrated for selective oxidation of alcohols to aldehydes and ketones in good yields. In the absence of any additives, the reaction was achieved by atmospheric air or molecular oxygen at room temperature.

Three Pd-decavanadates with a controllable molar ratio of Pd to decavanadate and their heterogeneous aerobic oxidation of benzylic C-H bonds

Huang, Xianqiang,Li, Jikun,Shen, Guodong,Xin, Nana,Lin, Zhengguo,Chi, Yingnan,Dou, Jianmin,Li, Dacheng,Hu, Changwen

, p. 726 - 733 (2017)

By the combination of Pd-complexes and [V10O28]6-, three Pd-decavanadate compounds [Pd(NH3)4]3[V10O28]·8H2O (1), [Pd(deta)(H2O)]2(NH4)2[V10O28]·2H2O (2) (deta = diethylenetriamine) and [Pd(dpa)2](Hdpa)2(Et3NH)2[V10O28]·2H2O (3) (dpa = 2,2′-dipyridylamine) have been successfully synthesized and thoroughly characterized using single X-ray diffraction (SXRD), powder X-ray diffraction (PXRD), infrared spectroscopy (FT-IR) and elemental analyses (EA). Interestingly, in the three compounds, the molar ratios of Pd to decavanadate vary from 3:1 to 1:1 by changing N-ligands. The three Pd-decavanadates as heterogeneous catalysts are active in the aerobic oxidation of benzylic hydrocarbons under solvent-free conditions without adding any additives and co-catalysts. Moreover, compound 1 can be reused three times without losing its activity.

Non-heme iron catalysts for the benzylic oxidation: A parallel ligand screening approach

Klopstra, Marten,Hage, Ronald,Kellogg, Richard M.,Feringa, Ben L.

, p. 4581 - 4584 (2003)

Ethylbenzene and 4-ethylanisole were used as model substrates for benzylic oxidation with H2O2 or O2 using a range of non-heme iron catalysts following a parallel ligand screening approach. Effective oxidation was found fo

Hydration of aromatic alkynes catalyzed by a self-assembled hexameric organic capsule

La Sorella, Giorgio,Sperni, Laura,Ballester, Pablo,Strukul, Giorgio,Scarso, Alessandro

, p. 6031 - 6036 (2016)

The combination of a Br?nsted acid catalyst and a supramolecular organic capsule formed by the self-assembly of six resorcin[4]arene units efficiently promotes the mild hydration of aromatic alkynes to their corresponding ketones. The capsule provides a suitable nanoenvironment that favors protonation of the substrate and addition of water.

In Situ Preparation of Au-SH@SO3H-SBA-15 Catalyst with Enhanced Activity and Durability in Alkyne Hydration

Zhu, Fengxia,Li, Hexing

, p. 1072 - 1076 (2014)

A facile approach was developed for synthesizing Au-SH@SO3H-SBA-15 with ordered mesoporous channels by reducing Au3+ to Au nanoparticles with SH-group bonded to silica support, followed by in situ coordinating Au with the unreacted SH-groups. This catalyst exhibited high efficiency in alkyne hydration owing to the high activity of uniformly dispersed ultrasmall Au nanoparticles, the diminished diffusion limit due to the mesoporous structure, and the promoting effect of acidic SO3H-groups resulting from oxidation of the SH-group by Au3+. Meanwhile, the catalyst could be easily recycled and displayed strong durability owing to the strong hydrothermal stability of mesoporous structure and the enhanced stability against Au leaching due to the Au-SH coordination bond.

Hydration of terminal alkynes catalyzed by a water-soluble salen-Co(III) complex

Wang, Shoufeng,Miao, Chengxia,Wang, Wenfang,Lei, Ziqiang,Sun, Wei

, p. 1695 - 1700 (2014)

A water-soluble salen-Co(III) complex was studied as catalyst for hydration of terminal alkynes to methyl ketones in the presence of H2SO4 as a co-catalyst. The products were obtained with excellent yields using relatively low catalyst loadings and a simple protocol. Notably, the products were easily separated from the catalyst after reaction by extraction, and the catalyst could be recovered and reused with only a slight loss of activity.

Pd(II)-Catalyzed Denitrogenative and Desulfinative Addition of Arylsulfonyl Hydrazides with Nitriles

Meng, Mengting,Yang, Liangfeng,Cheng, Kai,Qi, Chenze

, p. 3275 - 3284 (2018)

A Pd(II)-catalyzed denitrogenative and desulfinative addition of arylsulfonyl hydrazides with nitriles has been successfully achieved under mild conditions. This transformation is a new method for the addition reaction to nitriles with arylsulfonyl hydrazides as arylating agent, thus providing an alternative synthesis of aryl ketones. The reported addition reaction is tolerant to many common functional groups, and works well in the presence of electron-donating and electron-withdrawing substituents. Notably, the reported denitrogenative and desulfinative addition was also appropriate for alkyl nitriles, making this newly developed transformation attractive.

A well-defined complex for palladium-catalyzed aerobic oxidation of alcohols: Design, synthesis, and mechanistic considerations

Jensen, David R.,Schultz, Mitchell J.,Mueller, Jaime A.,Sigman, Matthew S.

, p. 3810 - 3813 (2003)

A breath of fresh air: A variety of alcohols are oxidized using 0.5-0.1 mol% of the catalyst, and in some cases the oxidation can simply be carried out open to the air (see scheme). Mechanistic insight into the mechanism is provided by a crystal structure that shows remarkable hydrogen bonds between the coordinated water and acetate ligands and an unprecedented large kinetic isotope effect.

Novel anti-Markovnikov regioselectivity in the Wacker reaction of styrenes

Wright, Joseph A.,Gaunt, Matthew J.,Spencer, Jonathan B.

, p. 949 - 955 (2006)

The Wacker reaction is one of the longest known palladium-catalysed organic transformations, and in the vast majority of cases proceeds with Markovnikov regioselectivity. Palladium(II)-mediated oxidation of styrenes was examined and in the absence of reoxidants was found to proceed in an anti-Markovnikov sense, giving aldehydes. Studies on the mechanism of this unusual transformation were carried out, and indicate the possible involvement of a η4-palladium-styrene complex. With a heteropolyacid as the terminal oxidant, oxidation of styrene to give the anti-Markovnikov aldehyde as the major product was found to be catalytic.

Identification of an ASE2 Mechanism in the Hydrolysis of Cyclic Thioacetals

Ali, Muhammad,Satchell, Derek P. N.

, p. 866 - 867 (1991)

2-Phenyl-2-methyl-1,3-dithiane and its p-methoxy derivative undergo hydrolysis in concentrated aqueous perchloric acid via the ASE2 mechanism rather than via the A1 mechanism.

Photohydration of Styrenes and Phenylacetylenes. General Acid Catalysis and Broensted Relationship

McEwen, John,Yates, Keith

, p. 5800 - 5808 (1987)

The acid-catalyzed photohydration of a series of substituted styrenes and phenylacetylenes have been investigated in aqueous buffer solutions.General acid catalysis was clearly detected in five cases with a range of catalysts, and approximately linear Broensted plots gave α values in the range 0.14-0.18.The rate enhancements caused by excitation from S0 to S1 were estimated from comparisons with thermal hydration data to be in the 1E11-1E15 range.Treatment of the dependence of the rate constants for general acid catalysis (kHA) on the buffer pKHA values with multiple regression analysis suggests that the Broensted plots are smoothly curved, as predicted by Eigen and by the Marcus equation.However, reliable values of the Broensted curvature could not be established.The possible catalytic reactivity analogous triplet states was examined with a series of nitrosubstituted analogues, but no general acid catalysis could be detected.The factors controlling the detection of general acid catalysis in these photoreactions are discussed.

Ruthenium carbonyl complexes with pyridine-alkoxide ligands: Synthesis, characterization and catalytic application in dehydrogenative oxidation of alcohols

Hao, Zhiqiang,Yan, Xinlong,Liu, Kang,Yue, Xiaohui,Han, Zhangang,Lin, Jin

, p. 15472 - 15478 (2018)

Several new trinuclear ruthenium carbonyl complexes chelated with 6-bromopyridine alcohol ligands, [6-bromopyC(CH2)4O]Ru3(CO)9 (1a), [6-bromopyC(CH2)5O]Ru3(CO)9 (1b), [6-bromopyC(Me)2O]Ru3(CO)9 (1c) and [6-bromopyCMeC6H5O]Ru3(CO)9 (1d), were synthesized by the reaction of Ru3(CO)12 with 6-bromopyC(CH2)4OH (L1H), 6-bromopyC(CH2)5OH (L2H), 6-bromopyC(Me)2OH (L3H) and 6-bromopyCMeC6H5OH (L4H) in refluxing THF, respectively. The free ligands L1H-L4H were synthesized by the nucleophilic reaction of lithium salt (generated from 2,6-dibromopyridine and n-BuLi) with the corresponding ketones. Furthermore, these pyridine-based ligands were characterized by NMR spectroscopy and elemental analyses. All the four ruthenium carbonyl complexes were well characterized by NMR, IR, single-crystal X-ray crystallography, etc. Complexes 1a-1d were found to exhibit high catalytic activities for the dehydrogenative oxidation of secondary alcohols to give their corresponding products in good to excellent yields.

Metal/catalyst/reagent free hydration of alkynes up to gram scale under temperature and pressure controlled condition

Ali, Munsaf,Srivastava, Avinash K.,Joshi, Raj K.

, p. 2075 - 2078 (2018)

A new green water-mediated metal/catalyst/reagent-free methodology for hydration of alkyne is devised. The remarkable yields of various ketones were achieved when alkynes were heated at 150 °C under 11 bar pressure in an autoclave for 14 h in water-methanol solution. Outstanding functional group compatibility for both the terminal and internal alkynes was established. This methodology produces excellent yields up to gram scale under optimised reaction condition.

-

Kosolapoff

, p. 1651 (1947)

-

Ruthenium-catalyzed oxidation of alkanes with tert-butyl hydroperoxide and peracetic acid

Murahashi,Komiya,Oda,Kuwabara,Naota

, p. 9186 - 9193 (2000)

The ruthenium-catalyzed oxidation of alkanes with tert-butyl hydroperoxide and peracetic acid gives the corresponding ketones and alcohols highly efficiently at room temperature. The former catalytic system, RuCl2(PPh3)3-t-BuOOH, is preferable to the oxidation of alkylated arenes to give aryl ketones. The latter system, Ru/C-CH3CO3H, is suitable especially for the synthesis of ketones and alcohols from alkanes. The ruthenium-catalyzed oxidation of cyclohexane with CH3CO3H in trifluoroacetic acid/CH2Cl2 at room temperature gave cyclohexyl trifluoroacetate and cyclohexanone with 90% conversion and 90% selectivity (85:15). The mechanistic study indicates that these catalytic oxidations of hydrocarbons involve oxo-ruthenium species as key intermediates.

Rh- and Ru-complex-catalyzed dimerization of arylethynes Rylethynes in aqueous environment

Novak, Petr,Kotora, Martin

, p. 433 - 442 (2009)

Complexes [RhCl(PPh3)3] and [Ru(CHPh)Cl 2(PCy3)2] efficiently catalyzed the dimerization of arylethynes to the corresponding 1,4-substituted enynes in aqueous environment in the presence of sodium dodecyl sulfate. The Rh catalyst exhibited almost exclusive preference for the formation of £-isomers, the Ru one exhibits strong preference for the formation of Z-isomers.

Microwave Heated Continuous Flow Palladium(II)-Catalyzed Desulfitative Synthesis of Aryl Ketones

Skillinghaug, Bobo,Rydfjord, Jonas,S?vmarker, Jonas,Larhed, Mats

, p. 2005 - 2011 (2016)

A protocol for Pd(II)-catalyzed desulfitative synthesis of aryl ketones from sodium aryl sulfinates and nitriles in continuous flow has been developed. The reactions proceed with microwave heating using microwave transparent tube reactors, affording the desired aryl ketones in fair to good yields. Microwave transparent aluminum oxide reactors were identified as a safe and thermostable alternative to borosilicate glass reactors.

Light-driven carbon dioxide reduction coupled with conversion of acetylenic group to ketone by a functional Janus catalyst based on keplerate {Mo132}

Lodh, Joyeeta,Mallick, Apabrita,Roy, Soumyajit

, p. 20844 - 20851 (2018)

Catalysts enabling CO2 reduction coupled with another organic reaction are rare. In this study, we report such a catalyst keplerate {Mo132}, which catalyses photochemical carbon dioxide reduction to formic acid coupled with organic transformation, i.e., hydration of phenylacetylene to acetophenone in visible light. It initially oxidizes water and injects the reducing equivalents for reduction of carbon dioxide at the same time, converting acetylenic group to ketone. Our designed redox Janus catalyst provides an inexpensive pathway to achieve carbon dioxide reduction as well as conversion of phenylacetylene to acetophenone, which is an industrially important precursor.

Clay supported ammonium nitrate 'Clayan': A mild and highly selective reagent for the deoximation of electron rich oximes

Meshram,Reddy, Gondi Sudershan,Srinivas, Dale,Yadav

, p. 2593 - 2600 (1998)

A simple and convenient method for selective deoximation of electron rich oximes is described using Clay supported ammonium nitrate 'Clayan'. Self destroying nature of the reagent makes the procedure attractive and eco- friendly.

Highly efficient oxidation of alcohols catalyzed by a porphyrin-inspired manganese complex

Dai, Wen,Lv, Ying,Wang, Lianyue,Shang, Sensen,Chen, Bo,Li, Guosong,Gao, Shuang

, p. 11268 - 11271 (2015)

A novel strategy for catalytic oxidation of a variety of benzylic, allylic, propargylic, and aliphatic alcohols to the corresponding aldehydes or ketones by an in situ formed porphyrin-inspired manganese complex in excellent yields (up to 99%) has been successfully developed.

Highly efficient AgBF4-catalyzed synthesis of methyl ketones from terminal alkynes

Chen, Zheng-Wang,Ye, Dong-Nai,Qian, Yi-Ping,Ye, Min,Liu, Liang-Xian

, p. 6116 - 6120 (2013)

A silver-catalyzed highly efficient synthesis of a wide range of methyl ketones from terminal alkynes is described. The reactions are conducted under convenient conditions and provide products with excellent regioselectivity in moderate to excellent yields, with broad substrate scope, including a variety of aromatic and aliphatic terminal alkynes.

Pd(II)-Mediated Oxidation of Olefine Using the Transannular Ozonides of 9-tert-Butylanthracenes as an Oxygen Atom Source

Matsuura, Akira,Ito, Yoshikatsu,Matsuura, Teruo

, p. 5002 - 5004 (1985)

-

Enantioselective oxidation of racemic secondary alcohols catalyzed by chiral Mn(III)-salen complex with sodium hypochlorite as oxidant

Zhang, Yuecheng,Zhou, Qiao,Ma, Wenchan,Zhao, Jiquan

, p. 114 - 117 (2014)

Chiral Mn(III)-salen complex catalyzed oxidative kinetic resolution (OKR) of secondary alcohols has been achieved with cheap and easily available sodium hypochlorite (NaClO) as oxidant. The novel protocol is very efficient for the OKR of a variety of secondary alcohols at room temperature.

Photophysics of Perylene Diimide Dianions and Their Application in Photoredox Catalysis

Li, Han,Wenger, Oliver S.

supporting information, (2021/12/23)

The two-electron reduced forms of perylene diimides (PDIs) are luminescent closed-shell species whose photochemical properties seem underexplored. Our proof-of-concept study demonstrates that straightforward (single) excitation of PDI dianions with green

Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy

Zhong, Jing,Zhou, Wuxin,Yan, Xufei,Xia, Ying,Xiang, Haifeng,Zhou, Xiangge

supporting information, p. 1372 - 1377 (2022/02/23)

A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.

Copper-Catalyzed Azide-Alkyne Cycloaddition of Hydrazoic Acid Formed in Situ from Sodium Azide Affords 4-Monosubstituted-1,2,3-Triazoles

Jankovi?, Dominik,Virant, Miha,Gazvoda, Martin

, p. 4018 - 4028 (2022/02/25)

We report a copper-catalyzed cycloaddition of hydrogen azide (hydrazoic acid, HN3) with terminal alkynes to form 4-substituted-1H-1,2,3-triazoles in a sustainable manner. Hydrazoic acid was formed in situ from sodium azide under acidic conditions to react with terminal alkynes in a copper-catalyzed reaction. Using polydentate N-donor chelating ligands and mild organic acids, the reactions were realized to proceed at room temperature under aerobic conditions in a methanol-water mixture and with 5 mol % catalyst loadings to afford 4-substituted-1,2,3-triazoles in high yields. This method is amenable on a wide range of alkyne substrates, including unprotected peptides, showing diverse functional group tolerance. It is applicable for late-stage functionalization synthetic strategies, as demonstrated in the synthesis of the triazole analogue of losartan. The preparation of orthogonally protected azahistidine from Fmoc-l-propargylglycine was realized on a gram scale. The hazardous nature of hydrazoic acid has been diminished as it forms in situ in a reactive species in the copper-catalyzed reaction.

A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination

Tang, Yu,Yu, Biao

, (2022/03/27)

A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.

PhSe(O)OH/NHPI-catalyzed oxidative deoximation reaction using air as oxidant

Shi, Yaocheng,Wang, Feng,Yang, Chenggen,Yu, Lei

, (2021/09/06)

A novel oxidative deoximation method was developed in this article. Compared with the reported organoselenium-catalyzed oxidative deoximation reaction, this reaction employed N-hydroxyphthalimide (NHPI) as the co-catalyst, so that the oxidative deoximation reaction could utilize air as oxidant in the green DMC solvent under mild reaction conditions. Control experiments and X-ray photoelectron spectroscopy (XPS) analysis results indicated that NHPI was essential for activating the catalytic organoselenium species. It could accelerate the activation of molecular oxygen in air to promote the reaction process. The reaction can avoid metal residues in product and is of potential application values in pharmaceutical industry due to the transition metal-free process.

Process route upstream and downstream products

Process route

acetic acid
64-19-7,77671-22-8

acetic acid

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
Conditions Yield
With iron(III) oxide; at 470 - 480 ℃;
Ketene
463-51-4

Ketene

methoxybenzene
100-66-3

methoxybenzene

2-Methoxyacetophenone
579-74-8

2-Methoxyacetophenone

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
Conditions Yield
With carbon disulfide; aluminium trichloride;
methoxybenzene
100-66-3

methoxybenzene

(E)-3-Ureido-but-2-enoic acid ethyl ester
5435-44-9,22243-66-9

(E)-3-Ureido-but-2-enoic acid ethyl ester

acetyl chloride
75-36-5

acetyl chloride

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
Conditions Yield
methoxybenzene
100-66-3

methoxybenzene

acetyl chloride
75-36-5

acetyl chloride

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
Conditions Yield
With aluminium trichloride; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride; at -10 ℃; for 0.25h;
99%
With zinc; at 80 - 82 ℃; for 0.00194444h; microwave irradiation;
99%
With indium(III) tosylate; In dodecane; nitromethane; for 1h; Schlenk technique; Reflux;
99%
With iron(III) oxide; at 20 ℃; for 0.0833333h; regioselective reaction;
98%
With iron oxide; In neat (no solvent); at 20 ℃; for 0.05h; Concentration; Reagent/catalyst; Solvent; Temperature; Time; Green chemistry;
98%
With zinc(II) oxide; at 20 ℃; for 0.0833333h;
97%
With InIII-based[In(OTf)3] Polymeric Sulfonic Acid Catalyst; In nitromethane; for 1h; Reagent/catalyst; Schlenk technique; Reflux;
97%
antimonypentachloride; N-benzyl-N,N,N-triethylammonium chloride; In nitromethane; at 120 ℃; for 0.333333h; Further Variations:; Catalysts; Temperatures; reusing run; Product distribution;
96%
With zinc oxide nanoparticles supported on polyaniline; at 20 ℃; for 0.166667h; Neat (no solvent);
96%
With cetyltrimethylammonim bromide; cetyltrimethylammonium chloride; In 1,2-dichloro-ethane; at 70 ℃; for 0.0833333h; Microwave irradiation; Micellar solution;
96%
With benzyltributylammonium tetrachloroferrate; at 50 ℃; for 0.0166667h;
95%
With aluminum (III) chloride; In dichloromethane; water; at -5 - 10 ℃; Temperature; Inert atmosphere;
93%
acetyl chloride; With aluminium trichloride; In 1,1,2,2-tetrachloroethane; at 0 ℃;
methoxybenzene; In 1,1,2,2-tetrachloroethane; at 0 - 20 ℃; Further stages.;
91%
With indium(III) triflate; lithium perchlorate; In nitromethane; at 20 ℃;
87%
With silver nitrate; In ethanol; at 20 ℃;
84%
With samarium (III) iodide; In acetonitrile; at 20 ℃; for 3h;
82%
With aluminium trichloride; for 2h; Heating;
80%
With o-tetrachloroquinone; (η5,η5-(C5H4)2SiMe2)Mo2(CO)6; In 1,2-dichloro-ethane; at 80 ℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique;
73.8%
With [Cp2Ti(OSO2C8F17)2]*2H2O*THF; In acetonitrile; at 20 ℃; for 4h; regioselective reaction;
70%
(p-MeOC6H4)2BSbCl6; In dichloromethane; for 24h; Ambient temperature;
53%
cobalt(II) chloride; In acetonitrile; for 12h; Ambient temperature;
50%
With carbon disulfide; aluminium trichloride;
With titanium tetrachloride;
With aluminium trichloride;
With aluminium trichloride;
With carbon disulfide; aluminium trichloride;
With aluminum (III) chloride; In chloroform; at 20 ℃; for 3h;
With Amberlyst-36; at 50 ℃;
With MoSi; at 80 ℃; for 10h; Reagent/catalyst; Temperature;
With copper(II) oxide; at 80 ℃; for 6h; Reagent/catalyst;
With aluminum (III) chloride; In dichloromethane; at 0 ℃; for 2h; Sealed tube; Inert atmosphere;
With aluminum (III) chloride; for 2h; Reflux;
58.6 g
methoxybenzene
100-66-3

methoxybenzene

3-(chlorocarbonyl)phenyl acetate
16446-73-4

3-(chlorocarbonyl)phenyl acetate

3-acetoxy-4'-methoxy-benzophenone
108897-14-9

3-acetoxy-4'-methoxy-benzophenone

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
Conditions Yield
With carbon disulfide; aluminium trichloride;
diethyl ether
60-29-7,927820-24-4

diethyl ether

methyllithium
917-54-4

methyllithium

4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
Conditions Yield
reagiert analog mit 4-Dimethylamino-benzonitril;
methyllithium
917-54-4

methyllithium

4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
Conditions Yield
methyl p-toluene sulfonate
80-48-8

methyl p-toluene sulfonate

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
Conditions Yield
With sodium hydroxide;
dimethyl sulfate
77-78-1

dimethyl sulfate

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
Conditions Yield
With poly(ethylene glycol) 400; sodium carbonate; at 110 ℃; for 10h;
96%
With lithium hydroxide; In tetrahydrofuran; at 70 ℃; for 1.5h;
90%
With alkali;
ethyl 4-methoxybenzoylacetate
2881-83-6

ethyl 4-methoxybenzoylacetate

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
Conditions Yield
With sulfuric acid;

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