Cyclohexanol, 4-1-butyl, trans

Cyclohexanedione, 46, 25 Cyclohexanimine, N-chloro-, 46,16 Cyclohexanol acetate, 46, 61 Cycloiiexanol, 4-1-butyl, trans-, 47,... 

An interesting example of etherification of close boiling cis and trans 2-tert-butyl-cyclohexanol with .v amylene may be cited. At 353 K, and Indian 130 as cataly.st at 10 % loading, about 94% selectivity for the cis isomer was realized with a feed consisting of about 68.5 % cis and 31.5% trcms isomer (Matkar and Sharma, 1995). 

HETHYL-1-PENTENE 4-METHYL-cis-2-PENTENE 4-METHYL-trans-2-PENTENE TRIETHYLENEDIAMINE BUTYL VINYL ETHER CYCLOHEXANOL... 

METHYL-trans-2-PENTENE TRIETHYLENEDIAMINE BUTYL VINYL ETHER CYCLOHEXANOL... 

Heptanol, 2-methyl-3-hexanol, 2,4-dimethyl-3-pentanol, cyclo-pentanol, cyclohexanol, cyclo-heptanol, cyclooctanol, cis-and trans-2-methylcyclohexanol, cis- and trans-4-tert-butyl-cyclohexanol ai2o3 180-210 94... 

OxUatiou of primary and secondary alcohals to carbonyl compounds. Corey and Kim report that the complex of N-chlorosuccinimide and dimethyl sulfide is somewhat superior to the complex of dimethyl sulfide and chlorine (this volume) for oxidation of primary and secondary alcohols the formation of hydrogen chloride is avoided and yields are generally higher. The procedure is illustrated for the oxidation of 4-r-butyl-cyclohexanol (2) to 4-r-butylcyclohexanonc (4). The complex (1) is prepared by addition of dimethyl sulfide (4.1 mmole) to a stirred solution of NCS (3.0 mmole) in toluene at 0° under argon. The mixture is cooled to -25° and a solution of 4-r-butylcyclo-hexanol (2.0 mmole, mixture of cis and trans) in toluene is added dropwise. The stirring is continued for 2 hr. at — 25° and then triethylamine (3.0 mmole) in toluene is added dropwise. The ketone (4) is obtained in almost quantitative yield. As in oxidation with the complex of dimethyl sulfide and chlorine, an intermediate sulfoxonium complex (3) is involved. 

Figure 1 Reaction scheme for the hydrogenation of 4-t-butyl phenol to cis and trans-4-t-butyl cyclohexanol.

The selective hydrogenation of 4-t-butyl phenol is of commercial interest for the manufacture of cis-4-t-butyl cyclohexanol (1), which as is an important product used in the Flavours and Fragrance industry. The reaction is also of interest in that several confounds are potential products of the reaction, namely the cis and trans-t-butyl cyclohexanol as well as the 4-t-butyl cyclohexanone. Previous studies (2, 3) have shown rhodium to be the most active catalyst for this reaction and... 

Materials. Propan-2-ol (Type A) was May Baker 2-propanol, either untreated or fractionated through a 30-inch Vigreux column. Propan-2-ol (Type B) was refluxed for 1 hour with sodium borohydride before fractionation. Both types had b.p., 82°C. Ethanol (b.p., 78°C.), methanol (b.p., 65°C.), tot-butyl alcohol (m.p., 25°C.), cyclohexanol (b.p., 161°C.), cyclohexane (b.p., 81°C.), and adamantane (m.p., 268°-270°C.) were purified by standard methods, cis- and trans-DecaMn were prepared by preparative gas-liquid chromatography (GLC), following removal of Tetralin by passing through silica gel. 

Finally, both methyllithium and methylmagnesium iodide added non-stereoselectively and at a considerably slower rate to the tert-butyl-cyclohexanone 27 (Fig. 1.5) at —80 °C, yielded in each case a mixture of both Cl epimers trans-A-ferf-butyl-cyclohexanol 28 and c 5-4-ferf-butyl-cyclohexanol 29. The isomer with the equatorial methyl group 28 (fra 5-product) was the predominant product in both reactions (28 29 = 3.6 1 in the first case and 3 1 in the second case). 

MeOH -PrOH iso-PrOH trans-4- /-butyl- cyclohexanol /-BuOH... 

Properties M.w. 156.27 sp.gr. 0.902 m.p. 43-46 C b.p. 209 C flash pt. 79 C Uses Fragrance in cosmetics Manuf./Distrib. ABCR http //www.abcr.de, Acros Org. http //www.acros.be-, Degussa http //WWW. degussa. com 4-t-Butylcyclohexanol CAS 98-52-2 EINECS/ELINCS 202-676-4 Synonyms 4-t-Butylcyclohexanol, cis and trans p-t-Butylcyclohexanol 4-t-Butylcyclohexanol, mixt. of isomers Cyclohexanol, 4-t-butyl- ... 

Butyl chloride 1-Chloronaphthalene Cyclohexane Cyclohexanol Cyclohexanone Cyclopentane cis-1,2-Dichloroethylene cis-trans-1,2-Dichloroethylene (mixed isomers) trans-1,2-Dichloroethylene Ethyl linoleate 2-Nitropropane... 

Spiniello, M., White, J. M. (2003). Low-temperature X-ray structural studies of the ester and ether derivatives of cis- and trans-4-tert-butyl cyclohexanol and 2-adamantanol apphcation of the variable oxygen probe to determine the relative a -donor ability of C-H and C-C bonds. Organic, Biomolecular Chemistry, 1, 3094—3101. This paper also provides an excellent historic survey of this problem. 

Lithium tri-i-amylborohydride is a generally more stereoselective reducing agent than the earlier reported lithium tri-s-butylborohydride. Thus 3-methyl- and 4-t-butyl-cyclohexanones yield trans-3-methyl- and cis-4-t-butyl-cyclohexanol respectively, in greater than 99.5% isomeric purity. In most hydride reductions of... 

Scheme 8.24. The reaction of 2-methylpropene (isobutylene [H2C=C(CH3)2]) with phosphoric acid to produce the f-butyl cation followed by the reaction of the latter with phenol (hydroxybenzene). Substitution occurs in the para-position. The resulting 4-(l-methylethyl) hydroxybenzene (4-f-butylphenol) is rednced with hydrogen (H2) in the presence of a platinum catalyst to produce ( )-(or trans-) r-butylcyclohexanol [( )- or (frons)-4-(l-methylethyl) cyclohexanol)].

N.m.r. and i.r. spectroscopy were used to identify" cis- and trans-4-t-butyl-[ 1 H]cyclohexane prepared from 4-t-butylcyclohexanone via the methanesulphonate of the intermediate [l- H]cyclohexanol compound. The resonances of the cis-and trans-isomers are located 5.98 and 5.42 p.p.m., respectively, above that of CDCI3. 

Carbonyl Reactivity.—A new reagent, lithium tri-s-butylborohydride, is claimed to exhibit enzyme-like stereoselectivity in reduction of cyclic (and bicyclic) ketones. Reduction of 2-methylcyclohexanone at 0°C in THF for 30 min occurred quantitatively to give the less stable cis-alcohol with an epimeric purity of 99.3%. 3,3,5-Trimethylcyclohexanone was reduced to the trans-alcohol with 99.8% stereoselectivity and 3-methylcyclohexanone likewise with 85% stereoselectivity. Reduction of 4-methylcyclohexanone to the cis-alcohol occurs with 80.5% stereoselectivity correspondingly cis-4-t-butyl-cyclohexanol is produced with 93% isomeric purity, much higher than in previous cited procedures, and this figure rises to 96.5% when reaction is... 

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