2-methyl-6-acetyl-naphthalene

Walther et al. improved the Na0Ph/C02 system by tuning the role of the solvent, such that the carboxylation of acetone was carried out selectively by sodium phenoxide with N-methyl-caprolactam under 0.1 MPa C02 to afford 3-ketoglutaric acid in 65% yield [34]. The same authors reported the conversion of acetyl-naphthalene (acetonaphthone) to acetyl-naphthalene carboxylic acid with 84% yield, and of cyclohexanone to cyclohexane-2,6-dicarboxylic acid in 56% yield. 

An oxidizable alkyl group is not necessarily attached to an aromatic nucleus. Oxidation of a methyl group of trimethylacetic acid by heating for 7 hours with alkaline permanganate gives dimethylmaIonic acid (35%). Other examples include the a-keto acids, trimethylpyruvic acid (40%) ° from pinacolone and /3-naphthylglyoxylic acid (40%) from -acetyl-naphthalene. 

The diphosphine on the left was used with a rhodium catalyst and hydrogen to reduce the dehydroamino acid derivatives. The same reduction could also be carried out with sugar-derived phosphinites, the product being obtained in 97-99% ee.84 The diphosphine on the right, or better its counterpart, in which isopropyl has replaced methyl, was used with a ruthenium catalyst and hydrogen or 2-propanol in the reductions of /3-ketoesters. 1-Acetyl-naphthalene was reduced with a ruthenium catalyst using the ligand on the left with 2-propanol (10.38) in more 99% yield and 97% ee. 

Methyl 2-naphthyl ketone. See 2 -Acetonaphthone Methyl a-naphthyl ketone CAS 941-98-0 EINECS/ELINCS 213-384-1 Synonyms 1-Acetonaphthalene 1-Acetonaphthone 1 -Acetonaphthone a-Acetonaphthone 1 -Acetyl naphthalene a-AcetyInpahthalene Ethanone, 1-(1-naphthalenyl)- Methyl 1-naphthyl ketone o-... 

Mercaptopropylmethyldimethoxysilane Mercaptopropyltrimethoxysilane 3-Methacryloxypropyltris (trimethylsiloxy) silane Methyl acetyl ricinoleate N-Methylaminopropyltrimethoxysilane 2-Methyl-1-butanol Methylcyclohexanol Methylcyclohexyldichlorosilane Methylcyclohexyldimethoxysilane Methyidichlorosilane Methyl palm kernelate Methylphenyidichlorosilane Methyltriacetoxysilane Methyltrichlorosilane Methyltridecylsilane Methyltriethoxysilane Methyltrimethoxysilane N-Methyl-N-trimethylsilyltrifluoroacetamide Methyltris (methylethylketoxime) silane Mica Microcrystalline cellulose Mineral oil Naphthalene Naphthenic acid Neatsfoot oil Nonoxynol-5 Octadecyidimethyl [3-(trimethoxysilyl) propyl] ammonium chloride Octadecyltrichlorosilane Octamethylcyclotetrasilazane Octamethylcyclotetrasiloxane Octamethyltrisiloxane Octaphenylcyclotetrasiloxane Octyidimethylchlorosilane 2-Octyl dodecanoic acid... 

Acetyl naphthalene 24 on photoirradiation undergoes [4 + 2]-cycloaddition reaction with chiral electron acceptor alkene, (5)-(2-methoxy methyl-1-... 

Naproxen, [(S)-6-methoxy ex -methyl 2-naphthalene acetic acid] is a non steroidal anti-inflammatory (NSAID), indicated for the treatment of rheumatoid, osteo and juvenile arthritis, as well as ankylosing spondylitis [16]. It is very useful for the relief of mild and moderate pain. Naproxen has also caused kidney problems and has sometimes caused blood pressure increases, especially for older people [17]. In the amperometric method, mercury [18] and Pt [19] have been used as the electrode materials of choice. However, mercury electrodes have some limitations as they are toxic and there is rapid deterioration of the electrode response. Conversely, the use of Pt electrodes shows high background current in the CV resulting in low S/B ratio with the addition of analyte and the linear dynamic range of concentrations is also very narrow. During the course of the synthesis of naproxen, other conditions such as pH, light and temperature may favor the formation of impurities such as 2-acetyl-6-methoxy naphthalene (AMN) (Scheme 1) in addition to naproxen, and it is very important to detect this compound precisely in both raw materials and final products. 

Acetoxylation and nitration. It has already been mentioned that 0- and m-xylene are acetoxylated as well as nitrated by solutions of acetyl nitrate in acetic anhydride. This occurs with some other homologues of benzene, and with methyl phenethyl ether,ii but not with anisole, mesitylene or naphthalene. Results are given in table 5.4. 

The nature of the aromatic substituents is apparently not critical for SSRI activity, as indicated by the structure of duloxetine (23-5), where one ring is replaced by thiophene and the other by naphthalene. The synthesis starts as above by the formation of the Mannich base (23-1) from 1-acetyl thiophene with formaldehyde and dimethyl-amine. Treatment of that intermediate with the complex from lithium aluminum hydride and the 2R,3S entantiomer of dimethylamino-l,2-diphenyl-3-methyl-butane-2-ol gives the S isomer (23-2) in high enantiomeric excess. Treatment of the aUcoxide from (23-2) and sodium hydride with 1-fluoronaphthalene leads to the displacement of halogen and thus the formation of ether (23-2). The surplus methyl group is then removed by yet another variant of the von Braun reaction that avoids the use of a base for saponifying the intermediate urethane. Thus, reaction of (23-3) with trichloroethyl formate leads to the A -demethylated chlorinated urethane (23-4). Treatment of that intermediate with zinc leads to a loss of the carbamate and the formation of the free secondary amine duloxetine (23-5) [23]. 

Synthesis of racemic naproxene Friedel-Crafts acylation (aluminum chloride - nitrobenzene) of p-naphthol methyl ether affords 2-acetyl-6-methoxy naphthalene, which, when treated with either dimethyl sulfonium or dimethylsulfoxonium methylide, gives 2-(6-methoxynaphthalen-2-yl)propylene oxide. Treatment of the latter with boron trifluoride etherate in tetrahydrofuran gives 2-(6-methoxynaphthalen-2-yl)propionaldehyde, which is oxidized using Jones reagent (4 M chromic acid) to yield the racemic 2-(6-methoxynaphthalen-2-yl)propionic acid. 

Alkenes add photochemically to naphthalenes, normally to give products from 1.2 addition to the ring. In a report which appears to be a further example of this reaction Chow and co-workers reveal that Irradiation of mixtures of naphthols. or their methyl ethers, and acetyl acetone yield products derived from 1,2 addition of the enol form of the diketone to the naphthalene ring. Thus 1-naphthol gives the cyclobutanol (109) which retro-aldolises to the isolated product (110). However, the authors show that the excited state involved is In... 

It was known that photoracemization of optically active sulfoxides can be induced upon sensitization with naphthalene [13]. Hence, by using (/ )-A -acetyl-1-naphthylethylamine 26 as a chiral sensitizer, the first photoderacemization of methyl p-tolyl sulfoxide 25a was performed to give an ee of 2.25% at the apparent photostationary state (pss) after prolonged irradiation [14]. However, more detailed examination, starting with 25a of 3.2% ee and 5.1% led to the conclusion that the ultimate value at the pss is 4.1% ee. With more a bulky substrate 25b, a higher ee of 12% was obtained upon photosensitization with (-f-)-W(trifluoro-methyl)-l-naphthylethylamine 27 [15]. 

Acetylation of naphthalene gives methyl naphthyl ketone, and sulfonation followed by alkaline fusion gives naphthol (Scheme 4.60). The methyl and ethyl ethers of naphthol are prepared from naphthol by reaction with the corresponding alkyl sulfate under basic conditions. These ethers are usually known by the shorter names of yara and nerolin, respectively. Yara, nerolin and methyl naphthyl ketone possess floral odours and are moderately important perfume ingredients. 

Ci2H10O, Mr 170.21, 6pi.7kPa 171-173 °C, df 1.171, ng° 1.6752, has been identified in some essential oils. It smells like orange blossom and is a colorless crystalline solid (mp 56 °C). It is usually prepared by Friedel-Crafts acetylation of naphthalene (with acetyl chloride, acetic anhydride, etc.) in the presence of aluminum chloride. In polar solvents (e.g., nitrobenzene), the percentage of the simultaneously formed a isomer is lower. Methyl P-naphthyl ketone is used in eau de cologne, soap perfumes, and detergents. It is a good fixative. 

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