Cyclohexanol methyl ether

Reaction of cyclohexene with mercury(II) acetate in CH3OH rather than H20, followed by treatment with NaBH4, yields cyclohexy) methyl ether rather than cyclohexanol. Suggest a mechanism. 

Preparation from hcxamethyldisiloxane and 12/AI powder in detail, followed by cleavage of cyclohexyl methyl ether, to give cyclohexanol (via the intermediate silyl ether). 

When an insufficient amount of iodotrimethylsilane was used by the submitters, cyclohexyl methyl ether remained at the end of the reaction and was eluted from the silica gel column before cyclohexanol. When present in the crude product, cyclohexyl iodide was also eluted from the column before cyclohexanol. 

CLEAVAGE OF METHYL ETHERS WITH lODOTRIMETHYLSILANE CYCLOHEXANOL FROM CYCLOHEXYL METHYL ETHER... 

B. Cyclohexanol from cyclohexyl methyl ether. In a 25-mL, oven-dried, round-bottomed flask is placed 1.722 g. (0.0151 mole) of cyclohexyl methyl ether (Note 7). The flask is purged with nitrogen and sealed with a rubber septum. By means of oven-dried syringes, 4 ml, of chloroform (Note 8), 0.5 g. (0.5 ml., 0.006 mole) of pyridine (Notes 8 and 9), and 4.8 g. (3.5 ml., 0.024 mole) of... 

Problem 14.55 Prepare the following ethers starting with benzene, toluene, phenol (C H OH), cyclohexanol, any aliphatic compound of three C s or less and any solvent or inorganic reagent a) dibenzyl ether, b) di-/i-butyl ether, (c) ethyl isopropyl ether, d) cyclohexyl methyl ether, (e) p-nitrophenyl ethyl ether, (/) divinyl ether (g) diphenyl ether. <... 

Water with aniline, benzene, benzyl alcohol, carbon disulphide, carbon tetrachloride, chloroform, cyclohexane, cyclohexanol, cyclohexanone, ether (particularly if acidified), ethyl acetate, isoamyl alcohol, methyl ethyl ketone, nitromethane, tributyl phosphate or toluene. 

FIGURE 8.8 Magnetic field dependence for the photolysis of a series of benzoyl containing molecules in cyclohexanol solution obtained by time-resolved infrared spectroscopy of the carbonyl group of the resulting benzoyl radical. Key 1 = a,a,a-trimethylacetophenone, 2 = 2-hydroxy-4-(2-hydroxyethoxy)-2-methylpropiophenone, 3 = 1-benzoylcyclohexanol, 4 = 2-hydroxy-2-methy Ipropiophenone, 5 = benzoin, 6 = methyl ether benzoin, 7 = dimethyl ether benzoin, 8 = 2-dimethylamino-2-(4-methyl-benzyl)-l-(4-morpholin-4-yl-phenyl)-butan-l-one. 

Methyl Cyclohexanol 28106-65-2 Tetrafluoropropanol 34590-94-8 Dipropylene Glycol Methyl Ether... 

Scheme 8.61. The reaction of an alcohol (cyclohexanol) with a chloromethyl ether, RO-CH2CI (R=CH3, chloromethyl methyl ether R=CeH5CH2, benzyl chloromethyl ether) to produce the corresponding acetal of methanal (formaldehyde).

Elimination of H2O from cycloalkanols and related processes One of the early cases of stereospecific fragmentation processes of gas-phase ions was the El-induced dehydration of stereoisomeric 4-sustitut-ed cyclohexanols. TransA-t-huty - and -4-arylcy-clohexanols 7t (Scheme 6) afford highly abundant [M-H20] ions, which are much less abundant in the mass spectra of the cis isomers 7c (Scheme 6). Similar stereospecificity has been also observed in the elimination of methanol and acetic acid from the corresponding methyl ethers and acetates. Deuterium labelling studies have shown that the H-atom from position 4 is abstracted in the course of the elimination of H2O from the m s-alcohols, but not to an appreciable extent in the case of the cis isomers. The low energy H-transfer from the tertiary... 

Cyclohexanol Cyclohexyl alcohol 94 QHi,0 Methyl teti-hutyl ether 107 C5H12O... 

C Nuclear magnetic resonance spectrum, acetaldehyde, 732 acetophenone, 732 anisole, 672 benzaldehyde, 732 benzoic acid, 771 p-bromoacetophenone, 449 2-butanone, 449, 732 crotonic acid. 771 cyclohexanol, 634 cyclohexanone, 732 ethyl benzoate, 477 methyl acetate, 443 methyl propanoate, 450 methyl propyl ether, 672... 

The formation of ethers such as 1806 by EtsSiH 84b can also be catalyzed by trityl perchlorate to convert, e.g., benzaldehyde in 84% yield into dibenzyl ether 1817 [48]. The combination of methyl phenethyl ketone 1813 with O-silylated 3-phenyl-n-pro-panol 1818, in the presence of trityl perchlorate, leads to the mixed ether 1819 in 68% yield [48] (Scheme 12.15). Instead of trityl perchlorate, the combination of trityl chloride with MesSiH 84a or EtsSiH 84b and sodium tetrakis[3,5-bis-(trifluoro-methyl)phenyl]borane as catalyst reduces carbonyl groups to ethers or olefins [49]. Employing TMSOTf 20 as catalyst gives very high yields of ethers. Thus benzaldehyde reacts with O-silylated allyl alcohol or O-silylated cyclohexanol to give the... 

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... 

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