1,3,5-Cyclohexanecarboxylic acid

Although turnover of the catalyst is low, even unreactive cyclohexane[526] and its derivatives are oxidatively carbonylated to cyclohexanecarboxylic acid using KiS Og as a reoxidant in 565% yield based on Pd(II)[527]. Similarly, methane and propane are converted into acetic acid in 1520% yield based on Pd(II) and butyric acid in 5500% yield [528],... 

N,N Dimethylcyclohexanecarboxamide A 500-ml three-necked flask is equipped with a reflux condenser (drying tube), a pressure-equalizing dropping funnel, and a magnetic stirrer. The flask is charged with 32 g (0.25 mole) of cyclohexanecarboxylic acid and thionyl chloride (45 g, 0.375 mole) is added over 5 minutes to the stirred acid. The flask is heated (oil bath) at a temperature of 150° for 1 hour. The reflux condenser is... 

Chemical Name trans-4-(aminomethyl)cyclohexanecarboxylic acid Common Name —... 

Ethyl 1-bromocyclohexanecarboxylate, when treated with magnesium in anhydrous ether-benzene with subsequent addition of cyclohexanone, yields ethyl l-(l-hydroxycyclohexyl)cyclo-hexanecarboxylate. Dehydration and saponification give rise to l-(l-cyclohexenyl)cyclohexanecarboxylic acid, which upon decarboxylation at 195° yields cyclohexylidenecyclohexane in 8% overall yield, m.p. 540.4 This olefin has also been prepared by the debromination of 1,1 -dibromobicyclohexyl with zinc in acetic acid. ... 

Carbonylation of alcohols to acids, table of examples, 46, 74 Carboxylation, by formic acid, 46, 74 of 2-methylcyclohexanol by formic acid-sulfuric acid to 1-methyl-cyclohexanecarboxylic acid, 46, 72... 

Cyclohexane, methylene-, 40, 66 Cyclohexanecarboxylic acid, 3,4,5-TRIACETOXY-, 42, 62 Cyclohexanecarboxylic acid, 3,4,5-iriol, 42, 62... 

Cyclohexane, methyl, 55, 112 CYCLOHEXANECARBOXYLIC ACID, 1 cyano-2-methyl-, ethyl ester, 55, 57 CYCLOHEXANONE, 2,3-epoxy- [7-Oxa-bityUo[4 1 0]heptan-2-one], 55, 52 2-Cyclohexen-l-one, 55, 52 5-Cyclohexene-l,4-dione, 2,3-dichloro-2,5-di-fm-butyl- [5-Cyclohexene-l,4-dione, 2,3-dichloro-2,5-bis( 1,1-di-methylethyl)-], 55, 32 5-Cyclohexene-l, 4-dione, 2,3,5-tnchloro-... 

The protocol is effective in preparation of hydrazides of 5 carbons or less. Cyclopropanecarboxylic acid hydrazide15 and isobutyric acid hydrazide16 were prepared from their corresponding acid chlorides in 64% and 71% yields, respectively. However, when this method was applied to cyclohexanecarboxylic acid chloride, the bis-acylhydrazide was the predominant product, and the mono-acylhydrazide17 was isolated in 25% yield.18... 

Cyclohexanecarboxylic acid hydrazide has low solubility in water. A biphasic mixture developed during the reaction, which led to the predominant formation of the bis-acylated material. 

Table 1. [53] Anodic decarboxylation of cyclohexanecarboxylic acid in different...

Dimethylamine (8) Methanamine, N-methyl- (9) (124-40-3) Methyl cyclohexanecarboxylate Cyclohexanecarboxylic acid, methyl ester (8, 9) (4630-82-4)... 

Blakley ER (1974) The microbial degradation of cyclohexanecarboxylic acid a pathway involving aromatiza-tion to form p-hydroxybenzoic acid. Can J Microbiol 20 1297-1306. 

Cyclohexanecarboxylic acid chloride, c351 Cyclohexaneethanol, c378 Cyclohexaneethyl acetate, c379 Cyclohexanemethanol, c384 Cyclohexanone cyanohydrin, hi 12 czis -4-Cyclohexene-l,2-dicarboximide, t82... 

The cyclohexanecarboxylic acid, m.p. 31-32°, purchased from Aldrich Chemical Company was used without further purification. 

A. cis- and trans-4-Aminocyclohexanecarboxylic acid. A mixture of 27.4 g. (0.20 mole) of />-aminobenzoic acid (Note 1), 200 ml. of water, and 2 g. of 10% rhodium-0.1% palladium on carbon ciitalyst (Note 2) is placed in a pressure bottle and hydrogenated at 50 p.s.i. When 0.6 mole of hydrogen has been absorbed (Note vl), the mixture is filtered and concentrated under reduced pressure until crystals start to form (Note 4). The mixture is diluted with 200 ml. of dimethylformamide and cooled to 5°, filtered, washed with dimethylformamide, then methanol, and amino-cyclohexanecarboxylic acid, m.p. 292-296° (Note 5). 

The quantity of hydrochloric acid used is normally insufficient to neutralize all the lithium hydroxide produced when the reaction mixture is quenched in the aqueous solution. As a result, any unchanged cyclohexanecarboxylic acid will be present as its lithium salt and will remain in the aqueous phase. 

Apart from the reaction of cyclohexanecarboxylic acid with methyllithium, cyclohexyl methyl ketone has been prepared by the reaction of cyclohexylmagnesium halides with acetyl chloride or acetic anhydride and by the reaction of methylmagnesium iodide with cyclohexanecarboxylic acid chloride. Other preparative methods include the aluminum chloride-catalyzed acetylation of cyclohexene in the presence of cyclohexane, the oxidation of cyclohexylmethylcarbinol, " the decarboxylation and rearrangement of the glycidic ester derived from cyclohexanone and M)utyl a-chloroj)ropionate, and the catalytic hydrogenation of 1-acetylcycIohexene. "... 

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