Cyclohexane 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],... 

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-... 

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. "... 

About 90% of the caprolactam is produced by the conventional cyclohexanone process. Cyclohexanone is obtained by catalytic oxidation of cyclohexane with air, or by hydrogenation of phenol and dehydrogenation of the cyclohexanol byproduct. The conversion of cyclohexanone to cyclohexanone oxime followed by Beckmann rearrangement gives caprolactam. About 10% of caprolactam is produced by photonitrosation of cyclohexane or by nitrosation of cyclohexanecarboxylic acid in the presence of sulfuric acid264. 

Alternatives to the use of hydroxylamine include the reaction of nit-rosylsulfuric acid with cyclohexanecarboxylic acid, obtained by the hydrogenation of benzoic acid, to produce s-caprolactam directly, and by the photochemical nitrosation of cyclohexane with NOCl, that yields cyclohexanone oxime hydrochloride. In both cases excess ammonium sulfate is also produced. 

CYCLOHEXANE see CPBOOO CYCLOHEXANECARBONITRILE, 5-OXO-l,3,3-TRIMETHYL- see IMG500 CYCLOHEXANECARBOXAMDE see CPB050 CYCLOHEXANECARBOXYLIC ACID, LEAD SALT see NAS500... 

CYCLOHEXANECARBOXYLIC ACID, TRIBUTYLSTANNYL ESTER see TIDIOO CYCLOHEXANEFORMAAODE see CPB050 cis-l,2,3,5-trans-4,6-CYCLOHEXANEHEXOL see IDE300 CYCLOHEXANE, ISOCYANATO-(9CI) see CPN500 CYCLOHEXANE, 5-ISOCYANATO-l-(ISOCYANATOMETHYL)-1,3,3-TRIMETHYL-(9CI) see IMGOOO... 

Cyclohexane, methyl-, 55, 112 CYCLOHEXANECARBOXYLIC ACID, 1-cyano-2-methyl-, ethyl ester, 55, 57 2-Cyclohexen-l-one, 55, 52 5-Cyclohexene-l, 4-dione, 2,3-dichloro-2,5-... 

Cyclohexamethyleneimine Cyclohexamethylenimine. See Hexamethyleneimine Cyclohexanamine. See Cyclohexylamine N-Cyclohexanamine. See Dicyclohexylamine Cyclohexanamine, N,N-diethyl-. See N,N-Diethylcyclohexylamine Cyclohexanamine, N,N-dimethyl-, compd. with a-isotridecyl-u)-hydroxypoly (oxy-1,2-ethanediyl) phosphate. See Isotridecyl alcohol, ethoxylated, phosphated, compd. with N,N-dimethylcyclohexanamine Cyclohexanamine, 4,4 -methylenebis-. See Bis (p-aminocyclohexyl) methane Cyclohexanamine, N-methyl-. SeeN-Methylcyclohexylamine Cyclohexancarboxylic acid. See Cyclohexanecarboxylic acid Cyclohexane... 

Cyclohexane, 1-trifluoromethyl-1,2,2,3,3,4,4,5,5,6,6-undecafluoro-. See Perfluoromethylcyclohexane Cyclohexanoic acid. See Cyclohexanecarboxylic acid Cyclohexanol... 

Cyclohexylmethane. See Methyl cyclohexane Cyclohexylmethanoic acid. See Cyclohexanecarboxylic acid N-Cyclohexylmethylamine. See N-Methylcyclohexylamine N-Cyclohexyl-4-methylbenzenesulfonamide. 

Asukamycin contains a second six-membered carbocyclic ring which is indeed derived from shikimic acid. The cyclohexane ring at the end of a short polyketide chain and its attached carbon are labeled by shikimic acid as well as by [carboxy- C]cyclohexanecarboxylic acid (Fig. 41). The same is true for the cyclohexanecarboxylic acid moiety... 

Show how cyclohexanecarboxylic acid could be synthesized from cyclohexane in good yield. 

Alkanes have been found to react with CO in the presence of Pd-based catalysts. Cyclohexane gives cyclohexanecarboxylic acid in 1981% yield based on Pd (4.3% based on cyclohexane) when reacted with CO with the Pd(0Ac)2/Cu(0Ac)2/K2S208/TFA catalytic system (Scheme 8). 

Scheme 3.10 Hydrocarboxylation of cyclohexane to cyclohexanecarboxylic acid (major product). Cyclohexanol and cyclohexanone are formed as by-products of oxidation.

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