N-Heptyl ether

Unsymmetrical ethers may be produced from the acid-promoted reactions of aldehydes and organosilicon hydrides when alcohols are introduced into the reaction medium (Eq. 173).327,328 An orthoester can be used in place of the alcohol in this transformation.327 335 A cyclic version of this conversion is reported.336 Treatment of a mixture of benzaldehyde and a 10 mol% excess of triethylsilane with methanol and sulfuric, trifluoroacetic, or trichloroacetic acid produces benzyl methyl ether in 85-87% yields.328 Changing the alcohol to ethanol, 1-propanol, 2-propanol, or 1-heptanol gives the corresponding unsymmetrical benzyl alkyl ethers in 45-87% yield with little or no side products.328 A notable exception is the tertiary alcohol 2-methyl-2-propanol, which requires 24 hours.328 1-Heptanal gives an 87% yield of //-lie ply I methyl ether with added methanol and a 49% yield of benzyl n-heptyl ether with added benzyl alcohol under similar conditions.328... 

Mono-ix-butyl ether pi-p. 81-2°. Mono-aeo.-wUyl ether m.p. 85-6°. Di-n-Myl edher m.p. 58°. Mono -n-heptyl ether i m.p. 82-3°. Di-n-heptyl ether m.p. 56°. Monio-n-oayl ether m.p. 88 . Di-n-oetyl ether m.p. W°. 

Prepare a Grignard reagent from 24 -5 g. of magnesium turnings, 179 g. (157 ml.) of n-heptyl bromide (Section 111,37), and 300 ml. of di-n-butyl ether (1). Cool the solution to 0° and, with vigorous stirring, add an excess of ethylene oxide. Maintain the temperature at 0° for 1 hour after the ethylene oxide has been introduced, then allow the temperature to rise to 40° and maintain the mixture at this temperature for 1 hour. Finally heat the mixture on a water bath for 2 hours. Decompose the addition product and isolate the alcohol according to the procedure for n-hexyl alcohol (Section 111,18) the addition of benzene is unnecessary. Collect the n-nonyl alcohol at 95-100°/12 mm. The yield is 95 g. 

Degradations of symmetrical long-chain dialkyl ethers are used to illustrate an entirely different metabolic pathway. The di-n-heptyl-, di-n-octyl-, di- -nonyl-, and di- -decyl ethers are degraded by a strain of Acinetobacter sp. to two different groups of metabolites (Figure 11.4) ... 

HEPTANOL 5-HETHYL-l-HEXANOL ISOPROPYL-TERT-BUTYL-ETHER n-HEPTYL MERCAPTAN BUTYL-PROPYL-SULFIDE ETHYL-PENTYL-SULFIDE HEXYL-METHYL-SULFIDE... 

Heptadecyl alcohol 3-Heptanol n-Heptyl acetate n-Hexyl ether Isoamyl acetate Methylbenzylamine... 

TABLE 17-2. STRUCTURE AND PHYSICAL PROPERTY RELATIONS FOI n-HEPTYL-SUBSTITUTED TERPHENYLS AND POLYPHENYL ETHERS... 

Persoonol dimethyl ether, the 3(Z)-alkene from Persoona elliptica has been synthesised (ref. 37) from 3,5-dimethoxybenzyl bromide by way of 4-(3,5-dimethoxyphenyl)but-1-yne which was alkylated with n-heptyl 4-toluenesulphonate followed by final reduction of the all ne product as shown in the scheme This method of preparation of the butyne was probably obligatory because of the inapplicability of the alkylation technique with 2-(3,5-dimethoxyphenyl)ethyl bromide due to its facile dehydrobromination. 

Di-pi-cyclopentadienylchromium. See Bis (cyclopentadienyl) chromium Di-pi-cyclopentadienyl cobalt. See Cobaltocene Dipias1 A. See Dibutyl phthalate Dipiast B. See Diisobutyl phthalate Dipiasi D. See Dioctyl adipate Dipiast E. See Di-n-heptyl phthalate Dipiast L8. See n-Dioc yl phthalate Dipiast N. See Diisononyl phthalate Dipiast O. See n-Dioctyl phthalate Dipiast R. See Diisodecyl phthalate Dipiast TM. See Tri-2-ethylhexyl trimellitate Dipiast TM8. See Trioctyl trimellitate Di (POE (4) lauryl ether) dimethyl ammonium chloride. See Dilaureth-4 dimonium chloride Di (POE (9) nonyl phenyl ether) citrate. See Dinonoxynol-9 citrate... 

Tri propylene glycol n-propyl ether solvent, aq. industrial coatings C8 alkyl acetate C9 alkyl acetate C10 alkyl acetate C13 alkyl acetate Oxo-heptyl acetate Oxo-hexyl acetate solvent, aq. inks Glyceryl formal solvent, aq. paints... 

A slight excess of hexamethyldisilane added slowly under argon to a suspension of Na-methoxide in 1 -dimethyl-2-imidazolidone (as basic aprotic solvent) containing n-heptyl chloride, and the product isolated after an additional hr. -> n-heptyltrimethylsilane. Y almost 100%. F. e., also with K-methoxide in the presence of 18-crown-6 polyether, s. H. Sakurai and F. Kondo, J. Organometal. Chem. 92, C46 (1975) crown ether diemistry, review, s. G. W. Gokel and H. D. Durst, Synthesis 1976, 168. 

Butanediol methyl ether acetate n-Heptyl alcohol... 

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