Methoxy-phenylacetic acid

200 grams of a/p/ia-tolunitrile and 800 cc. of concentrated hydrochloric acid are stirred for one hour at 50° C. then at 70° C. for five hours. After initial dissolution an oil separates. After six hours the mixture is cooled and diluted with 1500 cc. of water. The mixture is extracted repeatedly with ether. The combined ether extracts are distilled to dryness, phenylacetic acid being obtained. 

50 grams of 4-methoxy-a/p/ia-tolunitrile and 250 ccs. of concentrated hydrochloric acid are stirred at room temperature for 15 hours. 250 cc. of water are added slowly. The mixture is then heated with stirring to 70° C. for fifteen hours. After cooling, the solution is extracted with ether. The ether layer is evaporated. The residue is distilled in the vacuum. 4-methoxy-phenyl-acetic acid, B. P. 184-186° C. is obtained. 

Preparation of Homoveratric acid (3,4-Dimethoxy-phenylacetic acid) 

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The Step 2 product mixture was resolved using MA -dicyclohcxylcarbodiimide and ( S )-2-methoxy-2-phenylacetic acid. 

Procedure D [91] Mix the succinimide ester of (S)-2-methoxy-2-phenylacetic acid (2-10 mg), the amine (1 mg in 1 ml of THF) and water (1 ml) in a vial and heat the mixture on a steam bath for 15 min. Analyse the amides by direct injection, or partition into a suitable organic phase and dissolve in a more appropriate solvent. 

Reflux a mixture of 15 g. of homoanisamide, 30 g. of potassium hydroxide and 300 ml. of ethanol on a water bath for 5 hours. Dilute with 750 ml. of water, evaporate to 75 ml. and acidify to Congo red. Collect the acid and recrystallise it from ethyl alcohol. The yield of p-methoxy-phenylacetic acid, m.p. 86-87°, is 13 g. 

The (2R,3R,4R) diastereomer results from partial racemization of one or both of the allenylmetal intermediates. This point was confirmed by comparison to authentic material as the (S)-MPA ((S)-(2-methoxy)phenylacetic acid-Mosher s acid) derivative. The optical rotations of these compounds are small, and thus correlation by comparison of [ajp... 

In studies in man, less direct approaches are necessary and the concentrations of metabolites in CSF have been used to estimate central catecholamine turnover. Several GC-MS assays have been developed for the determination of homovanillic acid (HVA, 4-hydroxy-3-methoxy-phenylacetic acid), the major metabolite of dopamine [457,458,464,465]. 

Beilstein Handbook Reference) 2-(p-Anisyl)acetic acid Acetic acid, p-methoxyphenyl- Benzeneacetic acid, 4-methoxy- BRN 1101737 EINECS 203-1664 Homoanisic acid 4-Methoxybenzeneacetic acid 4-Methoxyphenylacetic acid p-Methoxy-phenylacetic acid NSC 27799. Used in manufacture of pharmaceuticals and other organic compounds. Plates mp = 87" bp2 = 138° 7.m = 225, 277, 283 nm (e = 9640,1700,1460, MeOH) slightly soluble in H2O (0.6 g/100 ml), CHCI3, ligroin, soluble in EtaO, CeHe, very soluble in EtOH LD50 (rat orl) = 1550 mg/kg. Lancaster Synthesis Co., Penta Ufg. 

A mixture of sodium p-methoxyphenylacetate (prepared from 5.56 g p-methoxy-phenylacetic acid and 7.20 g 25% methanolic sodium methoxide) and 2,4 -diacetoxybenzophenone was refluxed in 50 mL acetic anhydride for 40 h. When the solution was cooled to room temperature, it was poured into water and stirred for 2 h. The aqueous phase was removed by decantation, and the organic gum was dissolved in methylene chloride. This solution was washed in turn with aqueous-saturated NaHCOs, water, and brine and taken to dryness in vacuo. The residue was recrystallized once from methanol and twice from aqueous acetic acid to give 1.85 g 3-(p-methoxyphenyl)-4-(p-acetoxyphenyl)-coumarin. 

Preparation by reaction of o-methoxy-phenylacetic acid with resorcinol in the presence of boron trifluoride etherate under argon on a water bath for 1 h (98%) [5208]. 

Preparation by reaction of m-methoxy-phenylacetic acid with resorcinol under argon atmosphere,... 

Obtained by reaction of 3-hydroxy-4-methoxy-phenylacetic acid with pyrocatechol dimethyl ether in the presence of phosphoric acid [6272]. 

The stereochemistry of each enantiomer separated by the chiral HPLC has been studied after methanolysis of the epoxy ring. Examining the H NMR data of esters of the produced methoxyalcohols with (S)- and (R)-a-methoxy-a-(tri-fluoromethyl) phenylacetic acid by a modified Mosher s method [181], it has been indicated that the earlier eluting parent epoxides are (3S,4R)-, (6S,7R)-, and (9R,10S)-isomers (Table 7) [75, 76, 179]. The above three chiral HPLC columns show different resolution abilities but a different elution order is not observed. The resolution profile by the reversed-phase OJ-R column has been generalized with molecular shapes of the epoxy compounds considering the... 

The (S)-MTPACI is prepared by Mosher s method5 from (R)-a-methoxy-a-(trifluoromethyl)phenylacetic acid purchased from Aldrich Chemical Company, Inc. 

There are three types of chiral auxiliary that are used chiral derivatizing agents (CDAs), chiral lanthanide shift reagents (CLSRs) and chiral solvating agents (CSAs)75. Chiral derivatizing agents (CDAs), such as the enantiomers of o -methoxy-o -(trifluoromethyl)phenylacetic acid (MTPA, 83)76, require the separate formation of discrete... 

FIGURE 3. The NMR spectra of the two racemic diastereomers of lV-(4-methyl-2-pentyl)-a-methoxy-a-trifluoromethylphenylacetamide prepared from racemic a-methoxy-a-(trifluoromethyl)phenylacetic acid [MTPA, ( )-83] and racemic 4-methyl-2-pentylamine [( )-84] (A) 60-MHz proton spectrum in chloroform-4 with tetramethylsilane (TMS) as the internal standard (B) 94.1-MHz fluorine-19 spectrum in chloroform-4 with trifluoroacetic acid as the internal standard. Reprinted with permission from Reference 76. Copyright (1969) American Chemical Society... 

Dopamine metabolism was covered in the discussion of general catecholamine biochemistry. Dopamine is stored in synaptic vesicles, and this storage can be manipulated. Although the reuptake of released DA is the major deactivating mechanism, MAO and COMT act enzymatically on DA in the same way as on NE. However, following the degradative pathway of NE, DA will finally be metabolized to homovanillic acid (3-methoxy-4-hydroxy-phenylacetic acid), since it lacks the P-hydroxyl group. 

Aldrich Chemical Company, Inc., and were used without further purification. Dichloromethane used in the preparation of the Mosher ester was obtained from EM Science and was distilled from calcium hydride under a nitrogen atmosphere. (R)-(-)-a-Methoxy-a-(trifluoromethyl)phenyfacetyl chloride was prepared from (S)-(-)-a-methoxy-a-(trifluoromethyl)phenylacetic acid, as described in Note 21. 

Triethylamine (8) Ethanamine, N,N-diethyl- (9) (121-44-8) (R)-(+)-a-Methoxy-a-(trifluoromethyl)phenylacetic acid Hydratropic acid, p,p,p-trifluoro-a-methoxy-, (+)- (9) (20445-31-2)... 

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