Cyclohexyl methyl ether

We have shown that a number of aliphatic ethers, containing steric-ally accessible p-hydrogen atoms, are cleaved in good yield when the tetrahalogenoanthranilic acids are diazotised in ethers 128,59). Diethyl ether is cleaved to the tetrahalogenophenetole (90) and methyl-cyclohexyl ether affords the tetrahalogenoanisole. In this latter reaction we were able to detect cyclohexene and therefore a plausible, but as yet unproved, mechanism is as shown. 

Complex hydrides were used for reductions of organometallic compounds with good results. Trimethyllead chloride was reduced with lithium aluminum hydride in dimethyl ether at —78° to trimethylplumbane in 95% yield [1174, and 2-methoxycyclohexylmercury chloride with sodium borohydride in 0.5 n sodium hydroxide to methyl cyclohexyl ether in 86% yield [1175]. 

Kresge and Tobin48 also studied the hydrolysis of vinyl ethers and found a rate ratio of 130 between methyl vinyl ether and ethyl cA-trimethylsilylvinyl ether, corresponding to a stabilization of the /J-silyl carbocation of 2.9 kcal mol-1. In this case the small rate acceleration (compared to the cyclohexyl systems studied by Lambert) can be attributed to the unfavourable dihedral angle. The dihedral angle in the vinyl ether is 90° (24), and on protonation it drops to 60° (25), whereas maximum hyperconjugative interaction requires a dihedral angle of 0°. 

Answer VII-c is an unsymmetrical aliphatic etlicr (I -methyl cyclohexyl ethyl ether). 

Six more polyaryl ethers were made from 2,6-dichlorobenzonitrile (2) and one of the following monomers l,l -bis(4-hydroxy-3,5-dimethyl phenyl) cyclohexane 2,2 -bis (4-hydroxyphenyl) -2-phenyl ethane 1,3-bis(4-hydroxyphenyl)-1-ethyl cyclohexane 2- ( hydroxyphenyl)-2-[3-(4-hydroxyphenyl) -4-methyl cyclohexyl ] propane 2,2 -bis (4-hydroxy-3,5-dimethyl phenyl) propane and bisphenol A. 

Cyclohexanol Cyclohexyl alcohol 94 CeHi20 Methyl butyl ether 107 C4H13O... 

Mixed aliphatic ethers containing methyl or ethyl radicals can be synthesized from the corresponding alkyl sulfate and magnesium alcoholates, e.g., methyl n-butyl, methyl cyclohexyl, and methyl isoamyl ethers (70-78%). A higher yield of ethyl isobutyl ether is obtained by substituting sodium for magnesium (70% vs. 30%). ... 

If the alkyl group possesses any hydrogens, formation of alkene and alcohol predominates, whereas benzyl sulfite and like structures give the ether. Bordwell and Landis showed that the pyrolysis of methyl cyclohexyl sulfites parallels those of... 

Aky (C8-10) glycldyl ether monomer, actuate coatings Bis l[[4-(ethenyloxy) methyl] cyclohexyl] melhyU terephthalate Bis (4-vinyl oxy huiyt) hexanedlylbiscarbamate monomer, acrylate/epoxy coatings VEctomer VE 4051 monomer, acrylic polymers Methylacrylate monomer, acrylic resins Butyl methacrylate Hydroxypropyl methacrylate Isobutyl methacrylate monomer, acrylics... 

Bis((vinyloxy)methyl)cyclohexane. See 1,4-Cyclohexanedimethanol divinyl ether Bis [4-(vinyloxy) methyl] cyclohexyl] methyl] terephthalate. See Bis [[[4-(ethenyloxy) methyl] cyclohexyl] methyl] terephthalate Bis (4-vinylthiophenyl) sulfide CAS 152419-78-8 Synonyms MPV... 

Figure 5.13 Separation of phenolic antioxidants by thin-layer chromatography. Solvent benzene development distance 15 cm indicators (a) borate buffer (b) 0.1% 2,6-dichloro quinonechlorimide in methanol. 1 = hydroquinone monobenzyl ether 2 = 2,6-di-rerr-butyl-phenol 3 = 2,6-di-tert-butyl-4-methyl-phenol 4 = 2,6-di-tcrt-butyl-a-methoxy-4-methyl-phenol 5 = 2-a-methyl-cyclohexyl-4, 6-dimethyl-phenol 6 = butylated hydroxyanisole 7 = butylated hydroxy toluene 8 = 4,4"-bis (2,6-di-terf-butyl-phenol) 9 = 2,2"-methylene-bis (4-methyl-6-terf-butyl-phenol) 10 = 2,2"-methylene-bis (4-ethyl-6-fert-butyl-phenol) Reproduced from Kreiner and Warner, Journal of Chromatography [119]...

Carvacrol (1) Cyolohexene (0.5) Aids (0.16) — 25 3 Carvacryl cyclohexyl ether (15%), cydohexylcarvacrol (20%) 4r4-Amyl-2-isopropyl-5-methyl- 58... 

The (partial) description of the synthesis and coupling of the five fragments starts with the cyclohexyl moiety C —C. The first step involved the enantio- and diastereoselective harpless epoxidation of l,4-pentadien-3-ol described on p. 126f. The epoxide was converted in four steps to a d-vinyl d-lactone which gave a 3-cyclohexenecarboxylate via Ireland-CIaisen rearrangement (cf. p. 87). Uncatalysed hydroboration and oxidation (cf. p. 131) yielded the desired trans-2-methoxycyclohexanol which was protected as a silyl ether. The methyl car-... 

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

Yields of the primary alkyl acrylates vary somewhat, owing to occasional losses through formation of polymer, but are usually in the range of 85-99%. Some secondary alcohols react very slowly, others readily. The method has been applied to more than fifty alcohols, some of which (with percentage yields) are listed below ethyl, 99% isopropyl, 37% -amyl, 87% isoamyl, 95% -hexyl, 99% 4-methyl-2-pentyl, 95% 2-ethylhexyl, 95% capryl, 80% lauryl, 92% myristyl, 90% allyl, 70% fur-furyl, 86% citronellyl, 91% cyclohexyl, 93% benzyl, 81% (3-ethoxyethyl, 99% /S-(/3-phenoxyethoxy) ethyl (from diethylene glycol monophenyl ether), 88%. 

Ethers can often be prepared by SN2 reaction of alkoxide ions, RO-. with alkyl halides. Suppose you wanted to prepare cyclohexyl methyl ether. Which of the two possible routes shown below would you choose Explain. 

The reaction between 5-methyl-2-(l-methyl-1 -phenylethyl)cyclohexyl 2-oxoacetate and 2-buteny](tributyl)stannane promoted by boron trifluoride-diethyl ether complex showed a strong preference for 57-facial attack, with syn selectivity69. 

Cyclohexanone, 23,35 Cyclohexene oxide, 137 Cyclohcxyl methyl ether, 137 l-Cydohexyl-2-methylpropene, 68-9 ( )-l-Cyclohexyl-2-trimethyl ilylethene, 12 (Z)-l-Cyclohexyl-2-trimethylsilylelhene, 12 l-Cydohcxyl-2-trimethylsilylethyne, 12 (2-Cyclohexylidene-eihyl)trimethylsilane, 29 Cyclopentadec-2-ynone, 48 Cydopentadiene, 25 Cyclopentanone, 72 Cyclopentenones, 15 Cyclopropanone, 133... 

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... 

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