Methyl-2-methoxy-6- benzoate

The addition of two ortho-methyl groups to cumyl derivatives also results in a decrease in the Hammett reaction constant from p+ = —4.3 for cleavage of X-[8]-(4-nitrobenzoate) to p+ = —3.0 for cleavage of X-[10]-(4-methoxy-benzoate).27 This provides additional support for the conclusion that rotation about the CAr—Ca bond, which will minimize destabilizing steric interactions between methyl groups in the transition state, also reduces stabilizing resonance electron donation from the ring substituent to the benzylic carbon (Scheme 9). 

Madclung synthesis, 27-30 Mannich alkylation, 106, 119 7-mcthoxyindole, procedure for, 8 6-methoxyindole-3-carboxaldehyde, procedure for, 115 116 methyl 4-[5-(benzyloxycarbonyl)indol-3-yl]methyl-3-methoxy-benzoate, procedure for, 108... 

The trifluoromethoxybenzene group is not commonly found in herbicides. One exception is the herbicide trimefluor, which is prepared from methyl 4-methoxy benzoate in four steps (Fig. 23) [19], Trimefluor is a selective pre- and postemergence herbicide for use in cotton. 

FIGURE 3. Absorption of fluorescence spectra of MSA in methyl cyclohexane (solid lines) and fluorescence spectrum of methyl 2-methoxy benzoate in the same solvent (dashed) fluorescence spectra after Weller2. 

A second band in the ultraviolet region is indicated as a shoulder. The anomalously large Stokes shift of the blue band is not detected in methyl 2-methoxy benzoate (2) whose fluorescence has a maximum in the region of the weak ultraviolet band of MSA (Fig. 3). This behavior has been explained by Weller (1,2) on the basis of intramolecular proton transfer in the first excited singlet state according to the following ... 

In this case, the first choice derivative is the poro-methoxy benzoate, but for some alcohols, the best selectivity was obtained with the paro-methyl or ortho-methoxy ester [95]. This kind of approach has been exploited to solve practical problems, as shown for the enantiomers of an intermediate used for the synthesis of the chiral anticancer agent edatrexate [2, 87]. 

Potassium cyanate and methyl 3-methoxyanthranilate, left in cold, acidified aqueous solution overnight, deposited methyl 2-ureido-3-methoxy-benzoate, which, when boiled with water, cyclized to 8-methoxyquinazo-line-2,4-dione methyl 5-chloroanthranilate behaved similarly (no yields stated).257 2-Amino-3-ethoxycarbonyl-JV-methylpyridinium iodide, refluxed for 24 hr with potassium cyanate in dilute acetic acid, was converted in good yield to 8-methylpyrido[2,3-rf]pyrimidine (183).344... 

Figure 11.1. Molecular cores and chains mentioned in this chapter. Cores a = triphenylene, b — dibenzopyrene, c — hexahelicenetetrone, d = phthalocyanine, e — a-glucose, / = /i-glucose, g = tricycloquinazoline, h — truxene, i and j — phenanthrene, k — pyrene, I = dibenzoperylene, m = dibutyldibenzoperylene, n — metal bis-diphenylpropanedionate. Chains 3-methylalkanoate, 0-alkyllactate, 0-(7-methylalkyl)-glycolate, alkanoate, 3,7-dimethyloctyloxy, alkylthio, alkoxy, 3-methoxy-4-(7-methyl-alkoxy)-benzoate.

Methyl 4-hydroxy-3-methoxy-benzoate C9H-10O4 3943-74-6 182.173 nd (dll al) 64 286 s EtOH, peth si chi... 

Also obtained by UV light irradiation of 3-methoxy-5-methyl-phenyl benzoate in ethanol at 20° for 70 h (21%) [754]. 

Preparation by reaction of methyl isova-niUinate (methyl 3-hydroxy-4-methoxy-benzoate) with methylsulfinyle carbanion, itself obtained from DMSO and sodium hydride (89%) [5589]. 

Obtained by condensation of methyl 4-hydroxy-3-methoxy-benzoate with dimethylsulfone carbanion in DMSO (76%) [5584]. 

Ethyl p-methoxy-benzoate Ethyl p-methyl-benzoate Ethyl p-chloro-benzoate... 

An important question about the mechanism of acid catalyzed esterification concerns the origin of the alkoxy oxygen For example does the methoxy oxygen m methyl benzoate come from methanol or is it derived from benzoic acid s... 

Another example of enhanced sensitivity to substituent effects in the gas phase can be seen in a comparison of the gas-phase basicity for a series of substituted acetophenones and methyl benzoates. It was foimd that scnsitivtiy of the free energy to substituent changes was about four times that in solution, as measured by the comparison of A( for each substituent. The gas-phase data for both series were correlated by the Yukawa-Tsuno equation. For both series, the p value was about 12. However, the parameter r" ", which reflects the contribution of extra resonance effects, was greater in the acetophenone series than in the methyl benzoate series. This can be attributed to the substantial resonance stabilization provided by the methoxy group in the esters, which diminishes the extent of conjugation with the substituents. 

Eupe and Majewski attempted to determine by experiment the influence of the relative positions of osmophores on each other in the same molecule. In the case of the three methyl tri-azo-benzoates no great difference in the type of odour exists, only a difference in the strengths, the para compound being the strongest and the ortho the weakest. Of the three methoxy-acetophenones, as another example, the meta isomer is almost odourless in comparison with the ortho and para. 

Z, -2-METHOXY-l-PHENYLTHIO-l,3-BUTADIENE, 59,202 Methyl 2-(acetyloxy)benzoate, 56,63 METHYL 4-(ACETYLOXY)BENZOATE, 56,59... 

Mebeverine (81), a smooth muscle relaxant, is prepared, i. a., by reacting sodium 3,4-dimethoxy-benzoate (77) with 1,4-dichlorobutane to form chloro-ester 78 which is in turn transformed to the corresponding iodide (79) on heating with Nal in methyl-ethyl ketone. Alkylation of 2-ethylamino-3-p-methoxy-phenylpropane (80) with 79 leads to mebeverine... 

The authors chose pyruvic acid as their model compound this C3 molecule plays a central role in the metabolism of living cells. It was recently synthesized for the first time under hydrothermal conditions (Cody et al., 2000). Hazen and Deamer carried out their experiments at pressures and temperatures similar to those in hydrothermal systems (but not chosen to simulate such systems). The non-enzymatic reactions, which took place in relatively concentrated aqueous solutions, were intended to identify the subsequent self-selection and self-organisation potential of prebiotic molecular species. A considerable series of complex organic molecules was tentatively identified, such as methoxy- or methyl-substituted methyl benzoates or 2, 3, 4-trimethyl-2-cyclopenten-l-one, to name only a few. In particular, polymerisation products of pyruvic acid, and products of consecutive reactions such as decarboxylation and cycloaddition, were observed the expected tar fraction was not found, but water-soluble components were found as well as a chloroform-soluble fraction. The latter showed similarities to chloroform-soluble compounds from the Murchison carbonaceous chondrite (Hazen and Deamer, 2007). 

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