Cyclohexanecarbonyl chloride

Other methods for the preparation of cyclohexanecarboxaldehyde include the catalytic hydrogenation of 3-cyclohexene-1-carboxaldehyde, available from the Diels-Alder reaction of butadiene and acrolein, the reduction of cyclohexanecarbonyl chloride by lithium tri-tcrt-butoxy-aluminum hydride,the reduction of iV,A -dimethylcyclohexane-carboxamide with lithium diethoxyaluminum hydride, and the oxidation of the methane-sulfonate of cyclohexylmethanol with dimethyl sulfoxide. The hydrolysis, with simultaneous decarboxylation and rearrangement, of glycidic esters derived from cyclohexanone gives cyclohexanecarboxaldehyde. 

Cyclohexanecarbonyl chloride EK Triethylamine MCB, EK N-Methyl-A -nitroso-p-toluenesulfonamide A Isophorone MCB, A d < -Octalone-2 (Chapter 9, Section III)... 

Cyclohexanecarbonyl chloride was obtained from Eastman Organic Chemicals. 

Dipolar cycloaddition reactions, of nitrones to olefins, 46, 97 of 3-phenylsydnone, 46, 98 Dispiro[5.1.5.1]tetradecane-7,14-dione, photolysis to cyclohexylidene-cyclohexane, 47, 34 preparation from cyclohexanecarbonyl chloride and triethylamine, 47, 34 Displacement of bromine from 1-bromo-2-fluoroheptane to give 2-fluoro-heptyl acetate, 46, 37 N,N -Disubstituted formamidines from triethyl orthoformate and primary amines, 46, 41 N,N-Disubstituted thioureas from secondary amines and silicon tetra-isothiocyanate, 45, 69 N,N-Disubstituted ureas from secondary amines and silicon tetraiso-cyanate, 45, 69... 

Dispiro[5.1.5.1 ] te tradecane-7,14-dione, photolysis to cyclohexylidene-cyclohexane, 47, 34 preparation from cyclohexanecarbonyl chloride and triethylamine, 47, 34... 

Praziquantel Praziquantel, 2-(cyclcohexylcarbonyl)-l,2,3,6,7,llb-hexahydro-47f-pyrazino [2,la]isoquinolin-4-one (38.1.15), is a derivative of pyrazinoquinoline that is made in two ways [17-19], According to one of them, l-aminomethyl-l,2,3,4-tetrahydroiso-quinoline is alkylated with chloroacetic acid, and then the resulting amine is acylated with cyclohexanecarbonyl chloride to make l-(iV-carboxymethyl-iV-cyclohexylcarbonyl-aminomethyl)-l,2,3,4-tetra-hydroisoquinoline (38.1.14), which is heated at 150°C to give the desired praziquantel. 

N,N-Dimethylcyclohexanecarboxamide has been prepared by the action of dimethylamine on cyclohexanecarbonyl chloride.2 3> 7... 

Cyclohexanecarbonyl chloride. Use 91 g (0.7 mol) of cyclohexanecarboxylic acid and 166 g (1.4 mol) of thionyl chloride. Proceed as for hexanoyl chloride but heat under reflux for 2 hours. The yield of cyclohexanecarbonyl chloride is 100 g (78%), b.p. 76-78°C/12mmHg, after distillation through a Vigreux column. 

Such delocalization is not possible in cyclohexanecarbonyl chloride or any other aliphatic acid chloride. For this reason, aryl acid chlorides are usually less reactive toward nucleophiles than are aliphatic acid chlorides. 

Electroreduction of cyclohexanecarbonyl chloride (68) at a mercury cathode in acetonitrile leads to production of cyclohexanecarboxaldehyde (69) and 1,2-dicyclo-hexylethene-1,2-diol dicyclohexane carboxylate (70) as reduction products, reminiscent of phenylacetyl chloride ( equation 39). The isolation of small amounts of dicyclohexyl ketone (71) and dicyclohexylethanedione (72) strongly suggests that cyclohexanecarboxaldehyde is formed exclusively via an acyl radical intermediate65(equation 44). 

To a stirred solution of 3-methyl-1-propyluracil-5,6-diamine (0.80 g, 4.0 mmol) and pyridine (0.37 mL, 4.5 mmol) in anhyd CHjCl (10 mL) under argon at 5 °C was added cyclohexanecarbonyl chloride (0.56 mL, 4.1 mmol). After 15 min at 5 "C and 30 min at rt, the mixture was diluted with 0.5 M HCI and the layers separated. The aqueous layer was extracted with CHjCL (3 x 10 mL) and the combined organics were washed with sat. aq NaHCOj and dried (Na SO ). Concentration gave a yellow solid which was suspended in HjO (10 mL). NaOH (1.2 g, 30 mmol) was added and the mixture was refluxed for 30 min. The solution was cooled to rt, acidified to pH 2 with 5 M HCI, and stirred at rt for 30 min. The solution was left to stand overnight and then the resultant solids were collected, washed with H O (4 x 20 mL), and dried under vacuum at rt. Recrystallization (HjO) gave a fibrous white solid yield 0.73 g (62%) mp 189-191 °C. 

Electrogenerated nickel(I) salen has been used as a catalyst for the reductive intramolecular cyclizations of 6-bromo- and 6-iodo-l-phenyl-1-hexyne [338], the reduction of several Q ,ft)-dihaloalkanes [339], the reductive coupling of 2-bromo- and 2-iodoethanol to prepare 1,4-butanediol [340], the conversion of cyclohexanecarbonyl chloride to a tetramer [341], and the reduction of benzal chloride [342]. 

Acylation of 40 with cyclohexanecarbonyl chloride and tetrahydropyran-4-carbonyl chloride affords HOE-28637a (8a) and HOE-26961a (8b), respectively [50]. Similarly l-methyl-4-(pyrrolidin-l-ylcarbonyl)piperazine (9, CDRI 72-70) has been prepared by action of phosgene on 40 to get N-methylpiperazinecarbonyl chloride (43) followed by treatment with pyrrolidine [51] (scheme 2). 

Reagents (a) ClCOOEt, MeCOONa at pH 3.0-3.5, (b) Mel,(c) hydrolysis, (d) ClCONEt2, (e) HCOOH, HCHO (f) cyclohexanecarbonyl chloride or tetrahydropyran-4-carbonyl chloride, (g) COCI2 pyrrolidine (h) Ph2C03, (i) Et2NH. 

Intermolecular dehydrohalogenation [1, 1203, before references]. A solution of cyclohexanecarbonyl chloride (Eastman) in benzene is stirred and swept with... 

Cyclohexane Cyclohexaneaceticacid Cyclohexanecarbonitrile Cyclohexanecarbonyl chloride Cyclohexanecarboxaldehyde... 

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