4-Methylphenyl methyl ether

To 2-methylphenol in aq. NaOH at 5-10° ethyl fluoro-sulphonate added with vigorous stirring and mixture heatedat 40° for 0.5h., to give 2-methylphenyl methyl ether. 

Beilstein Handbook Reference) Benz-ene, 1-methyl-3-phenoxy- BRN 2045714 EINECS 222-716-4 Ether, phenyl m-tolyl- 1-Methyl-3-phenoxy-benzene 3-Methyldiphenyl ether 3-Methylphenyl phenyl ether m-Methylphenyl phenyl ether Phenoxytoluene m-Phenoxytoluene Phenyl m-tolyl ether. Liquid bp 272° d25n1,051. 

CAS 100-66-3 El NECS/ELINCS 202-876-1 UN 2222 (DOT) FEMA 2097 Synonyms Benzene, methoxy Ether, methyl phenyl Methoxybenzene Methylphenyl ether Phenol methyl ether Phenyl methylether Classification Ether Empirical C7H8O Formula CHaOCeHs... 

Methylbenzoic acid methyl ester. See p-Cresyl acetate Methyl p-toluate Methyl benzoin. See Benzoin methyl ether Methylbenzol. See Toluene 2-Methyl benzophenone CAS 131-58-8 EINECS/ELINCS 205-032-0 Synonyms 2-Benzophenone, methyl- (2-Methylphenyl) phenylmethanone Phenyl tolyl ketone Phenyl-o-tolyl-methanone Classification Aromatic ketone Empirical C14H12O... 

Irisolone methyl ether 4, 5-Dimethoxy-6J-methylenedioxyisoflavone, 1494 Isobutyrylmallotojaponin. l-[3-[(3-Acelyl-2,4-dihydroxy-6-methoxy-5-methylphenyl)-methyl]-2,4,6-trihydroxy-5-(3-methyl-2-butenyl)phenyl]-2-methyl-1-propanone, 1644... 

Baeckeol methyl ether. 2-Methyl-l-(2,4,6-trimethoxy-3-methylphenyl)-l-propanone, 2046... 

CiiHijNO, 3SS4J-4J-7) see Carboquone 2-(2-aminocarbonyloxy-l-methoxyethyl)-S-methyl-hydroquinone dimethyl ether (CjjHiijNOj 38843-63-9) see Carboquone [6U-[6a,7a,7(iJ )])-3-[[(aminocarbonyl)oxyJmethyl]-7-[[5-carboxy-S-[[(4-methylphenyl)sulfonyl]amino]-l-oxo-pentyl]amino]-7-methoxy-8-oxo-5-thia-l-azabicy-clo[4.2.01oct-2-ene-2-carboxylic acid compd. with A-cyclohexylcyclohexanamine (1 1)... 

In a related series of 1,2,4-trisubstituted anthraquinone compounds, the effectiveness of various polar and nonpolar substituents to improve on the low heat fastness of 2-amino-1,4-dihydroxyanthraquinone (3.184 R = H) was examined (Table 3.50). Short-chain alkyl groups (methyl, ethyl) and even the pyranylmethyl ether are relatively ineffective but hydroxyalkyl, cyclohexyl, benzyl and morpholinylethyl groups show moderate increases. Further improvement is given by phenyl, pyridylmethyl and morpholinylpropyl. Outstandingly effective, however, are the benzothiazolyl, dodecylphenyl and fluoro-methylphenyl groupings. 

Dimethylamino)methyl]-5-methylphenyl]lithium is a white crystalline solid and is pyrophoric in air. Furthermore, it is soluble in hydrocarbons and ethers. Molecular weight determinations in benzene have established a tetrameric structure.12 In THF, like [2-[(dimethylamino)-methyl]phenyl]lithium, this tetramer breaks down to a dimeric species. 

Conversion into 6-methyl-2-(4-methylphenyl)hepta- 1,5-diene. 2- 4-methyl-phenyl)prop-2-enyl vinyl ether. A mixture of the foregoing allylic alcohol (2.5 g), ethyl vinyl ether (75 ml) and freshly crystallised mercury(n) acetate (600 mg) is refluxed continuously for 12 hours on a water bath. The reaction mixture is chilled in ice and mixed with 10 per cent aqueous sodium carbonate solution (25 g) and stirred well for 30 minutes at 0 °C. The organic layer is... 

To a solution of ethyl trifluoroacetate (1.90 ml, 16.0 mmol) in 7 ml of methyl tert-butyl ether was added 25% NaOMe (3.62 ml, 16.8 mmol). Next 4-chloroaceteophenone (2.08 ml, 16.0 mmol) in 2 ml of methyl tert-butyl ether was added. The mixture was stirred at room temperature overnight. To above solution was added 100 ml of 90% EtOH, followed by 4 N HCI (4.0 ml, 16 mmol) and 4-sulphonamidophenylhydrazine hydrochloride (3.58 g, 16 mmol). The mixture was heated to reflux for 3 hours. The mixture was concentrated. When 30 ml of water was added, a solid formed. The solid was filtered and washed with 20 ml of 60% EtOH to give 4.50 g of white solid. The filtrate was evaporated and taken up in ethyl acetate (100 ml), washed with saturated NaHC03, and brine, dried over MgS04, and concentrated. Heptane was added at boiling point of the mixture. After cooling down to 0°C, 1.01 g more product was obtained. The combined yield of the 4-(5-(4-methylphenyl)-3-trifluoromethyl-N-pyrazol-l-yl)benzenesulfonamide (Celecoxib) was 86%. 

Allylphenols and derivatives with substituents in the allyl group can, be prepared by direct C-alkylation of the sodium salt of the phenol in benzene solution.16 This method is not as good for the preparation of allylphenols themselves as the one involving preparation of the allyl ether followed by rearrangement, because a mixture of several products is obtained in C-alkylation. Thus the alkylation of p-cresol in benzene with sodium and allyl bromide yields 20% of allyl 4-methylphenyl ether, 8% of allyl 2-allyl-4-methylphenyl ether, 40% of 2-allyl-4-methyl-phenol, and 15% of 2,6-diallyl-4-methylphenol.16 The rearrangement of allyl 4-methylphenyl ether, however, yields 2-allyl-4-methylphenol in practically quantitative yield, and the ether is easily obtained. 

Methylphenylimino)methyl]phenyl Tellurium Bromide A solution of 1.60 g (10 mmol) bromine in 40 ml chloroform are added dropwise to the vigorously stirred solution of 3.80 g (10 mmol) butyl 2-(4 -methyIphenylimino)methylphenyl tellurium in 40 ml chloroform. The mixture is heated to the boiling point and then cooled. The mixture is filtered to remove a small amount of the aryl tellurium tribromide. The filtrate is concentrated to 20 ml and then mixed with 20 ml dry diethyl ether. The yellow crystals arc collected by filtration, washed with diethyl ether, and dried yield 92% m.p. 170°. 

The catalytic hydrosilylation of acetophenone or t-butyl methyl ketone with diethyl-, methylphenyl- or diphenylsilane in the presence of rhodium(I) catalysts containing (R,i )-(-l-)- or (S,S)-(—)-170, followed by acid cleavage of the intermediate silyl ethers, affords the respective alcohols with optical yields of 10—42% . The synthesis of (ff)-(-l-)-l-phenylethanol from acetophenone and diethylsilane in conjunction with the catalyst derived from (S,S)-( —)-170 was the most effective reaction (equation 28). In... 

The scope of this reaction with respect to the 2-arylpyridine includes substrates with ortho substituents such as 3-methyl-2-phenylpyridine, 2-(2-methylphenyl) pyridine, and 2-(l-naphthyl)pyridine that result in singly arylated C-H/C-M coupling products. The sensitivity of this reaction to sterics is further evidenced by the selective phenylation of 2-(2-naphthyl)pyridine at the 3-naphthyl position while the more sterically hindered 8-naphthyl position is unreactive. Both electron-neutral (Ph4Sn) and electron-rich ((4-MeOC6H4)4Sn) tetraarylstannanes have been shown to participate in this reaction, but the reaction with ortho substituted and/or sterically hindered stannanes has not been demonstrated. Functional group tolerance for groups other than aryl ethers has not been reported. 

E)- and (Z)-4-Benzyloxy-3-hydroxy-l-(4-methylphenyl)-l-butene gave, with triethyl orthoacetate in the presence of pivalic acid, the same, but enantiomeric, (R,E) and (.S , )-6-benzyloxy-3-(4-methylphenyl)-4-hexenoate [5 65%, 87% ee from the (E -butene R 78%, 90% ee from the (Z)-butene] (see p 3374)288. Similarly, (R,E)- and (S, )-6-benzyloxy-3-(4-methylphenyl)-4-hexenal are obtained by heating the (E)- and (Z)-butenes with excess methyl vinyl ether in the presence of mercury(II) acetate in a sealed tube [S 72 %, 90 % ee from the (E)-butene R 71 %, 85% ee from the (Z)-butcnc]288. Analogous strategies have been used to construct the phytyl side chain of tocopherol (see p 3370)289,290. 

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