Cyclohexanecarboxylic acid methyl ester

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

C8H14O3 cis-2-hydroxy-cyclohexanecarboxylic acid methyl ester 936-03-8... 

C9H16O3 cis-2-methoxy-cyclohexanecarboxylic acid methyl ester 13640-65-8... 

C11H20O2 1-propyl-cyclohexanecarboxylic acid methyl ester 4630-86-8... 

C20H38O2 cis-4-methyl-cyclohexanecarboxylic acid dodecyl ester 110746-60-6... 

C11H20O2 1-methyl-cyclohexanecarboxylic acid propyl ester 6739-35-1... 

C11H20O2 1-methyl-cyclohexanecarboxylic acid isopropyl ester 6553-86-2 ... 

C16H30O2 cis-4-methyl-cyclohexanecarboxylic acid octyl ester 101433-97-0... 

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. "... 

CYCLOHEXANECARBOXYLIC ACID, l-cyano-2-methyl-, ethyl ester, 55,... 

For more remote substitution p is expected to be smaller. Thus Hay and Porter-28 found p = 0.6 for the alkaline hydrolysis of the methyl esters of a-amino acids, RCH(NH2)COOCH.3 in water at 25°C. However, higher sensitivities are possible if the geometry of the system is such that the direct transmission of polar effects becomes more important. For example, Roberts and Moreland245 found that the effects of substituents in the 4 position of ethyl bicyclo-[2.2.2]octane-l-carboxylates (28) on the hydrolysis in 88% ethanol at 30°C are comparable to those observed for meta- anti para-substituted benzoates (p = 2.24), and a similar, though smaller, effect, is observed for methyl rrarts-4-substituted cyclohexanecarboxylates (29). 

Methyl 2-oxocyclohexanecarboxylate Cyclohexanecarboxylic acid, 2-oxo-, methyl ester (9) (41302-34-5)... 

METHYL-4-(l-ETHENYL-l-METHYL)-, irons- [24655-72-9], 61, 112 CYCLOHEXANECARBOTHIOIC ACID, S-(U-DIMETHYLETHYL) ESTER [54829-37-7], 61, 48, 134 Cyclohexanecarboxylic acid [98-89-5], 61, 134 CYCLOHEXANECARBOXYLIC ACID, K77-BUTYL ESTER, 61, 48 CYCLOHEXANECARBOXYLIC ACID. 1,1-DIMETHYLETHYL ESTER [16537-05-6], 61, 48... 

The strain energy of the cyclopropane ring is determined from thermochemical measurements on two closely related compounds the /r-butyl ester of cyclopropanecarboxylic acid and the methyl ester of cyclohexanecarboxylic acid. Both compounds can be synthesized from the appropriate acid chlorides, and their heats of combustion measured with a bomb calorimeter. 

Siegel, S. and Komarmy, J.M. (1960). Quantitative Relationships in the Reactions of trans-4-X-Cyclohexanecarboxylic Acids and their Methyl Esters. J.Am.Chem.Soc., 82,2547-2553. 

The HF-SbFs system works well in the Gattermann-Koch formylatlon of arenes and the Koch carbonylation of alkanes [54]. For instance, biphenyl is diformylated in HF-SbFs-CO to afford 4,4 -diformylbiphenyl as a major isomer (Scheme 14.20). The carbonylation of alkanes with C5-C9 carbon atoms in the HF-SbFs-CO system affords mixtures of C3-C8 carboxylic acids after hydrolysis of the generated secondary carbenium ions [55]. Successive treatment of methylcyclopentane with CO in HF-SbF and with water produces cyclohexanecarboxylic acid as a major product (Scheme 14.21) [56]. It seems that a tertiary methylcyclopentyl cation readily isomerizes to the more stable cyclohexyl cation before being trapped by CO. Bicyclic a, -unsaturated ketones are functionahzed by HF-SbF or FSOsH-SbFs under a CO atmosphere to give saturated keto esters after methanolysis (Scheme 14.22) [57]. Alcohols with short carbon chains also react with CO in HF-SbFs to give the corresponding methyl esters [58]. y-Butyrolactones are carboxy-lated under the same conditions to afford 1,5-dicarboxyhc acids [59]. 

Diederich s group has reported some bis-coenzyme models in which the thiazolium ring was a pendant on a macrocyclic system, that in the presence of MeFl in methanol converted aliphatic and aromatic aldehydes to the corresponding methyl esters. According to the mechanism in Scheme 1, the aldehyde is added to the ylide via to produce HEThDP-type compounds, then is deprotonated (Ar. ) to the enamine, that is oxidized to 2-acylThDP, that in turn is deacylated using methanol and resulting in the methyl ester. The principal novelty of the report is the ability to electrochemically recycle the reduced MeFlH". The yield of aromatic methyl esters, especially with electron-withdrawing para substituents, was much superior to that of the aliphatic esters of valeric and cyclohexanecarboxylic acids. 

Cyclohexanecarboxylic acid, 2,2-dimethyl-2,4-dioxo-3-(1-((2- propenyloxy)amino)butylidene)-, methyl ester, sodium salt Alloxydim-sodium 3633, 4271a ... 

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-... 

Scheme 9.147. A representation of the reaction between the methyl ester of cyclohexanecar-boxylic acid (methyl cyclohexanecarboxylate) with lithium diisopropylamide (LDA) to generate a carbanion on the carbon a- to the carbonyl. The carbanion so formed then acts as a nucleophile toward methyl iodide (CH3I) to yield methyl 1-methylcyclohexanecarboxylate, lithium iodide, and recovered base, diisopropylamine ([(CH3)2CH]2NHj.

Substitution processes focused around the carbonyl group as well as at the carbonyl group are, of course, also possible. Consider the case depicted in item 7 of Table 9.9. As noted immediately above for the intermolecular and intramolecular versions of the Claisen condensation, success depends upon generation of an anion a- to the carbon of the carbonyl. Generation of such anions, particularly at fairly high dilution (where reaction between esters is less likely) with hindered bases, followed by addition of an electrophilic species to the reaction medium, results in overall substitution of the electrophilic species for the proton that was removed. In item 7 of Table 9.9, as shown in Scheme 9.147, the methyl ester of cyclohexanecar-boxylic acid (methyl cyclohexanecarboxylate) does not react with the hindered base (LDA) at the carbon of the carbonyl. Rather, the base removes the proton on the carbon a- to the carbonyl and the carbanion so formed then acts as a nucleophile toward methyl iodide (CH3I). Substitution yields methyl 1-methylcyclohexanecarboxylate, lithium iodide, and recovered base, diisopropylamine [(CH3)2CH]2NH. ... 

N -butyllithium in hexane added at -15 to -10° under Ng to a stirred soln. of diisopropylamine in tetrahydrofuran, after 15 min. treated dropwise with a soln. of methyl cyclohexanecarboxylate in tetrahydrofuran, then a fast CO2-stream introduced for 10 min. cyclohexane-1,1-dicarboxylic acid monomethyl ester. Y 97%. F. e. and limitations s. S. Reiffers, H. Wynberg, and J. Strating, Tetrah. Let. 1971, 3001 s. a. A. J. H. Klunder and B. Zwanenburg, ibid. 1972, 2383. 

C15H26O2 cyclohexanecarboxylic acid (l-methyl-cyclohexyl)-methyl ester ... 

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