4- methylbenzoate

Radical 7 can subsequently fragment to fonn methyl radical (8) and methylbenzoate (9). 

The 7V-methylbenzo[( e]quinoline 426 was prepared by trapping the insertion product of an internal alkyne with a tertiary dimethylamine. One methyl group is eliminated. The dimethylaminonaphthalene-Pd complex 427 is an active catalyst and other Pd compounds are inactive[290a]. 

Because cyano groups may be hydrolyzed to carboxylic acids (Section 20 19) the Sand meyer preparation of aryl nitriles is a key step m the conversion of arylammes to sub stituted benzoic acids In the example just cited the o methylbenzomtnle that was formed was subsequently subiected to acid catalyzed hydrolysis and gave o methylbenzoic acid in 80-89% yield... 

These esters are prepared from the diazomethylpyrenes and carboxylic acids in DMF (R = H, 60% yield, R = Me, 80% yield, R = Ph, 20% yield for 4-methylbenzoic acid). They are cleaved by photolysis at 340 nm (80-100% yield, R = H). The esters are very fluorescent ... 

In order to remove 1-3 g. of contaminating 2-hydroxy-3-methylbenzoic acid, the crude acid is ground in a mortar and refluxed briefly with 100 ml. of chloroform, and the suspension is filtered hot (Note 9). The separated solid is dried in air and added to 1 1. of boiling water. Fhe mixture is boiled gently for 15 min-... 

Hydroxyisophthalic acid has been prepared by oxidizing 2-hydroxy-3-methylbenzoic acid with lead dioxide, by cleaving the ether group of 2-methoxyisophthalic acid with hydriodic acid, and by hydrolyzing 2-iodoisophthalic acid with alcoholic sodium hydroxide. ... 

In the synthesis of the twelve-membered ring, LiC104 was used as a templating ion and the methylbenzo-12-crown-4 (mp 46—48°) was obtained in 15% yield. Alpha-bro-mination was effected in 70% yield and conversion to the bridged species occurred in 20% and 25% yield when n = lor n = 2 respectively. 

The tautomeric structure leads to ambiguities in the nomenclature of compounds in this series. Thus, 5-methyl- and 6-methylbenzo-furoxan denote two different molecules which, because of their interconversion, cannot be isolated separately at normal temperatures. Throughout this review, when we intend to refer to the ambiguous mixture, we shall use the system employing the lowest numbers. The above methyl derivative, for example, will be described as 6-methyl-benzofuroxan regardless of the form adopted in the crystal. When a... 

An excellent method for producing methyl indole-4-carboxylate from commercially available 3-nitro-2-methylbenzoic acid involves reduction of an intermediate nitroenamine (57). 

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