M-Anisic acid

Dinitro-(m-anisic) Acid, col ndls(from w), mp 195°(Ref 2), l99°(Ref 3). Can be prepd by oxidation of 2,6-dinitro-3-methoxybenzalde-hyde with aq KMnO, soln(Refs 2 3)... 

Amino-benzyl alcohol m-Toluic acid m-Anisic acid... 

Tuning of selectivity in the metallation of m-anisic acid has been realized by an appropriate choice of base.67 The results obtained with LTMP have indicated that the regiochemistry of the lithiation of m-anisic acid is thermodynamically controlled. Resonance and inductive effects favour removal of the H(2) proton. In contrast, superbases such as n-BuLi-r-BuOK are not significantly influenced by or//m-directing groups and preferentially attack H(4), the inductively activated aromatic position next to the most electronegative heteroatom and/or the most acidic position available. 

Again m-anisic acid demand is yet not established. Some quantities are consumed in Japan and China. Current consumption is estimated at 25-30 tpa. 

H.74) Benzoic acid, 4-hydroxy-3-methoxy-, 4-hydroxy-3-methoxybenzoic acid, p-vanillic acid, vanillic acid, 4-hydroxy-m-anisic acid [121-34-6]... 

An additional useful test is to distil the acid or its sodium salt with sodalime. Heat 0.5 g. of the acid or its sodium salt with 0 2 g. of soda lime in an ignition tube to make certain that there is no explosion. Then grind together 0 - 5 g. of the acid with 3 g. of soda lime, place the mixture in a Pyrex test-tube and cover it with an equal bulk of soda lime. Fit a wide delivery tube dipping into an empty test-tube. Clamp the tube near the mouth. Heat the soda lime first and then the mixture gradually to a dull-red heat. Examine the product this may consist of aromatic hydrocarbons or derivatives, e.g., phenol from salicylic acid, anisole frx>m anisic acid, toluene from toluic acid, etc. 

CAS 617-05-0 EINECS/ELINCS 210-503-9 Synonyms m-Anisic acid, 4-hydroxy-, ethyl ester Benzoic acid, 4-hydroxy-3-methoxy-, ethyl ester Ethyl 4-hydroxy-3-methoxybenzoate Ethyl 3-methoxy-4-hydroxybenzoate 3-Methoxy-4-hydroxybenzoic acid, ethyl ester... 

Preparation by reaction of m-anisic acid with 3-methoxyphenol in the presence of zinc chloride and phosphorous oxychloride at 65-70° for 2 h (54%) [1136]. 

Obtained (poor yield) by condensation of m-anisic acid with resorcinol in the presence of zinc chloride at 160° for 10 min (Nencki reaction) (4%) [1137]. m.p. 176° [1137] Spectra (NA). 

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