5-ethyl-2-methoxyphenol

Ethyl-methoxyphenol Xylopia aethiopica (Annonaceae) [fruit] OD-R (smokey)... 

Chemically, wood tar is a complex mixture that contains at least 200 individual compounds, among which the foUowing have been isolated (1) 2-methoxyphenol, 2-methoxy-4-ethylphenol, 5-meth5i-2-methoxyphenol, 2,6-x5ienol, butyric acid, crotonic acid, 1-hydroxy-2-propanone, butyrolactone, 2-methyl-3-hydroxy-4JT-pyran-4-one, 2-methyl-2-propenal, methyl ethyl ketone, methyl isopropyl ketone, methyl furyl ketone, and 2-hydroxy-3-methyl-2-cyclopenten-l-one. 

The palladium-catalyzed substitution of the less reactive racemic ethyl 3-cyclohexe-nyl carbonate could, in a similar fashion, be completed with dimethyl malonate, p-methoxyphenol, or phthalimide as nucleophiles, with satisfactory ee (Eq. 11.38) [55]. These reactions, when irradiated for 1 min with temperatures up to 100 °C, delivered yields (91-96%) and ee values (94—95%) identical with those performed in... 

The intermolecular reaction of phenols with propiolic esters occurs in the presence of a Pd(OAc)2 catalyst to afford coumarin derivatives directly.48,48a An exclusive formation of 5,6,7-trimethoxy-4-phenylcoumarin is observed in the Pd(OAc)2-catalyzed reaction of 3,4,5-trimethoxyphenol with ethyl phenylpropiolate in TFA (Equation (46)). Coumarin derivatives are obtained in high yields in the cases of electron-rich phenols, such as 3,4-methylenedioxyphenol, 3-methoxyphenol, 2-naphthol, and 3,5-dimethylphenol. A similar direct route to coumarin derivatives is accomplished by the reaction of phenols with propiolic acids (Equation (47)).49 A similar reaction proceeds in formic acid at room temperature for the synthesis of coumarins.50,50a Interestingly, Pd(0), rather than Pd(n), is involved in this reaction. 

In addition to MMA, a variety of methacrylic esters were polymerized rapidly to the corresponding polymers with narrow MWDs in the presence of methylaluminum bis(2-ferf-butyl-4-methoxyphenolate) (3c). The successful examples include ethyl methacrylate (EMA), isopropyl methacrylate ( °PMA), n-butyl methacrylate ("BMA), isobutyl methacrylate ( °BMA), benzyl methacrylate (BnMA), and dodecyl methacrylate (Cj2MA), where the Mn values were all close to the predicted values (Mn j ) with the Mw/Mn ratios below 1.1 (Table 3, runs 1-4,6,7). The polymerization of ferf-butyl methacrylate ( BMA) is the only exception, where the monomer conversion hardly increased even after 24 h. 

Dimethylthexylsilyl trifluorometh-anesulfonate, 74 using other methods Allyl chloroformate, 9 Benzyl trichloroacetimidate, 32 Bromodimethylborane, 47 Chloromethyl ethyl ether, 75 2,3-Dihydro-1,4-dioxin, 112 p-Methoxyphenol, 181 of aldehydes and ketones as acetals or dithioacetals... 

SYNTHESIS To a solution of 12.3 g 3-ethoxy-4-methoxyphenol (see recipe for MEM for the preparation of this phenol) in 20 mL MeOH, there was added a warm solution of4.8gKOH in 100 mL MeOH. There was then added 8.2 g ethyl bromide, and the mixture held at reflux on the steam bath. Within 0.5 h, severe bumping ensued. An additional 3 g ethyl bromide were added, refluxing continued for... 

SYNTHESIS To a solution of 14.0 g 4-ethoxy-3-methoxyphenol (see the recipe for MME for the preparation of this starting material) in an equal volume of EtOH, there was added a solution of 5.3 g KOH in 100 mL hot MeOH. This was followed with 9.1 g ethyl bromide, and the mixture was held at reflux for 2 h. The first deposition of KBr was apparent in 5 min, and there was rather severe bumping by the end of the reaction. The mixture was diluted with 3 volumes H20 and 1 volume 5% NaOH, and extracted with 2x200 mL Et20. The extracts were pooled, and the solvent removed under vacuum, yielding 14.3 g of a pale amber oil that set to crystals of 2,5-diethoxyanisole with a mp of 44-45 °C. The compound had been reported in the literature from the action of diethyl sulfate on methoxyhydroquinone. 

A solution of 14 g of the distilled, solid 4-ethoxy-3-methoxyphenol in 20 mL MeOH was treated with a solution of 5.3 g KOH in 100 mL hot MeOH. There was then added 11.9 g methyl iodide, and the mixture was held at reflux temperature for 2 h. The reaction was quenched with 3 volumes H.O, made strongly basic by the addition of 1 volume of 5% NaOH, and extracted with 2x150 mL E O. Pooling the extracts and removal of the solvent under vacuum gave 9.7 g of 2.4-dimethoxy-1-ethoxybenzene as a clear, off-white oil that showed a single peak by GC. An acceptable alternate synthesis of this ether i s the ethylation of 2,4-dimethoxyphenol, whichisdescribedintherecipeforTMA-4. The index of refraction was nD25 = 1.5210. 

From the molecular beam MS of the pyrolysis products of the P/N fractions, a number of phenolic compounds were detected guaiacol (2-methoxyphenol) (m/z 124), catechols (m/z 110), isomers of substituted 2-methoxyphenols with alkyl groups such as methyl (m/z 138), vinyl (m/z 150), 3-hydroxy-propen(l)-yl (m/z 180), allyl (m/z 164), hydroxyethyl (m/z 168), and ethyl (152), most likely in the para position. In addition, a few carbohydrate-derived components are also present in this fraction such as furfuryl alcohol and other furfural derivatives. 

The decomposition of lignin into aromatic repeat units is a long practiced art that reached its zenith around 1800 a.d. Production of chemicals by wood pyrolysis was extensively practiced until, between 1750 and 1850 a.d., coal slowly displaced wood as the major chemical source available to man. Wood is usually pyrolyzed at 260-4 lO C and lignin at 300-440 C to produce 50 wt % charcoal, 10-15% tar, and lesser amounts of 2-propanone, ethanoic acid, and methanol [16-181. The tar is often called wood creosote and is a complex mixture of substituted phenols and aromatics. It contains phenol, 2- and 4-methylphenol, 2,4-dimethylphenol, 2-methoxyphenol, 4-methyl-2-methoxyphenol, and 4-ethyl-2-methoxyphenol [19]. 

Rayne, S., Eggers, N.J. (2007a). Quantitative determination of 4-ethylphenol and 4-ethyl-2-methoxyphenol in wines by a stable isotope dilution assay. J. Chromatogr. A, 1167, 195-201. 

The intrinsic viscosity of each polymer was determined by dilute solution viscometry using distilled methyl ethyl ketone as the solvent at a constant temperature of 30 C. The MEK was distilled onto p-methoxyphenol to prevent peroxide formation. 

H.35) (H.35) Phenol, 4-ethyl-2-methoxy-, 4-ethyl-2-methoxyphenol, 4-ethylguaiacol [2785-89-9]... 

Ethyl-2-methoxyphenol Ethyl (4-methoxyphehyl)acetate Ethyl 2-methylacetoacetate AEEthyl-2-methylallylamine 5-Elliyl-5-(2-methylallyl)-2-thiobarbituricacid... 

The yield of methoxyphenols from anisole varies with the initial molar proportion of NBNH to ferric ion reaching a maximum at a 1 1 ratio. The 590-m/x absorption of the ferric-NBNH complex in ethyl alcohol shows a similar variation with the proportion of ferric ion to NBNH. A possible reaction scheme is outlined in Scheme 2. 

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