Heptyl aldehyde

Heptanal. Heptaldehyde Aldehyde C-7 heptyl-aldehyde oenantbal enamhal oenanthol oenanthaldehyde enanthaldehyde. CjH1(0 mol wt 114.18. C 73.63%, H... 

HEPTYL ALDEHYDE. CHj(CH2>5 CHO. Aluminum alloy separators, rectifier tanks, and storage tanks have b n used with both crude and refined... 

Pyrolytic Decomposition. The pyrolytic decomposition at 350—460°C of castor oil or the methyl ester of ricinoleic acid spHts the ricinoleate molecule at the hydroxyl group forming heptaldehyde and undecylenic acids. Heptaldehyde, used in the manufacture of synthetic flavors and fragrances (see Elavors and spices Perfumes) may also be converted to heptanoic acid by various oxidation techniques and to heptyl alcohol by catalytic hydrogenation. When heptaldehyde reacts with benzaldehyde, amyl cinnamic aldehyde is produced (see Cinnamic acid, cinnamaldehyde, and cinnamyl... 

It has been frequently noted that certain lots of iron filings are not satisfactory for the reduction of heptaldehyde to heptyl alcohol in acetic acid solution. E. E. Reld and J. R. Ruhoff have found that the addition of a solution of 20 g. of nickel cliloride hexahydrate in 50 cc. of water immediately after the addition of the aldehyde will cause the reaction to start at once and wiU greatly accelerate the rate of reaction so that it is complete in two hours instead of the usual six to seven hours. The checkers have found this to be the case even with a lot of iron which could not be made to react when reduced in hydrogen. It is also recommended that the reaction mixture be divided between two 12-I. flasks and that 3 1. of water be added to each half immediately at the end of the reaction. This prevents the mixture from setting to a hard mass in case the steam distillation is not carried out at once, and also reduces the amount of foaming. 

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... 

Heptyl 3-Phenylpropyl Ether [Electrogenerated Acid-Promoted Reduction of an Aldehyde to an Unsymmetrical Ether].333 A mixture of 1-heptanal (1.0 mmol), 3-phenylpropoxytrimethylsilane (1.2 mmol), tetra-n-butylammonium perchlorate (0.1 mmol), and lithium perchlorate (0.1 mmol) was dissolved in CH2CI2 (3 mL) in an undivided cell. The mixture was electrolyzed under constant current (1.67 mA cm-2) with platinum electrodes at ambient temperature. After 5 minutes, dimethylphenylsilane (1.2 mmol) was added drop-wise and the electrolysis was continued (0.06 Faraday/mol). After completion of the reaction, one drop of Et3N was added and the solution was concentrated. The residue was chromatographed on Si02 to give 1-heptyl 3-phenylpropyl... 

A similar sequence was used to synthesize C-3 alkyl derivatives using the corresponding aldehydes for hydroxy-alkylation (Scheme 46). Exposure of the hydroxy acetals 420 to TEA and hydroquinone in dichloromethane at room temperature afforded 3-methyl, 3-phenyl, and 3-heptyl furoindoles 421. The overall yields of the 3-alkyl furoindoles 421 from indole were 46-63% <2002JOC1001>. 

Fatty Decanal Ethyl nonanoate Heptyl alcohol Lauryl alcohol, aldehyde Nonanal Octanal l-Octanol Undecanal 10-Undecenal. 

Preparation of b/s(5-pivaloxypentyl)zinc by iodine-zinc exchange and its enantioselective addition to an aldehyde preparation of (6SI-6-hydroxy-7-(triisopropylsiloxy) heptyl pivalate19... 

Alkyl Formate Production. In the past few years, formate esters have become an important class of organic compounds mainly because of their versatility as chemical feedstock (16,36-42), and as raw materials for the perfume and fragrance industry (43-46). Specifically, formate esters (methyl, ethyl, pentyl, etc.) have been used as starting material for the production of aldehydes (36), ketones ( ), carboxylic acids (37-40), and amides ( ). For example, methyl formate can be hydrolyzed to formic acid (39,40) or catalytically isomerized to acetic acid ( ). On the other hand, alkyl formates have been employed in the perfume and fragrance industry in amounts of approximately 1000 to 3000 Ib/year (43—46). Among the formates that have been commonly used for these purposes are octyl ( ), heptyl ( ), ethyl ( ), and amyl ( ) formates. 

Cyclopentanone readily undergoes aldol condensation with a variety of aldehydes to give the 2-alkylidenecyclopentanones (Scheme 4.66). These have jasmine-like odours, but are no longer used in perfumery since it was discovered that they have the potential to cause skin sensitization. The saturated products are safe and are used to give jasminic, fruity, floral odours in fragrances. The most widely used are the H-heptyl- (R = pentyl) and -hexyl- (R = butyl) derivatives. These are sold under tradenames such as Heptone and Jasmatone , respectively. 

Attempts to extend this methodology to a-sulfinyl derivatives of other esters have been only moderately successful. As shown in Scheme 14, ester (215) may be deprotonated by r-butylmagnesium bromide and added to aldehydes, although not to ketones. The intermediate P-hydroxy-a-sulfinyl esters, in each case a mixture of diastereomers, are reduced to obtain diastereomeric mixtures of -hydroxy esters. The diastereomeric ratio of these materials does not reveal the degree of asymmetric induction in the original aldol reactions, because of the unknown stereochemistry of the desulf urization step. Aldols (216) were converted by a three-step process into secondary alcohols (217), which were found to have isomeric purities of 33.5% enantiomeric excess for R = Ph and 80% enantiomeric excess for R = n-heptyl. 

CM-2,6-dialkyl-2//,6/f-l,3,5-oxaselenazines (237) are synthesized from selenoamides, aldehydes (236 R = methyl, heptyl, or t-butyl), and boron trifluoride etherate (Equation (56)) <90CL913>. 

The stereoselectivity of the reaction of 1 -alkynylzinc bromides 130 (R == heptyl or Ph) with various chiral a-benzyloxy aldehydes 131 (R = Me, /-Pr or PhCH20CH2) to yield the alcohols 132 depends on the nature of the substituents R and R Regiospecific propargylation with acylsilanes is exemplified by the reaction of the organozinc bromide 133 (from 2-octynyl bromide and zinc dust in THF) with benzoyltrimethylsilane, followed by desilylation, to yield only the alcohol 134 . 

Aliphatic and aromatic aldehydes react with carbon tetrabromide and triphenylphosphine to yield 1,1-dibromoalkenes 156, which are converted into alkynes 157 by the action of butyllithium or lithium amalgam. A convenient modification of the second step is the use of magnesium metal in boiling THF. 1-Chloro-l-alkynes 159 (R = Bu, hexyl, heptyl etc.) are produced from aldehydes and carbon tetrachloride/triphenylphosphine/magnesium, followed by dehydrochlorination of the products 158 with potassium hydroxide in the presence of the phase-transfer agent Aliquat 336. ... 

Because of their interest in products with liquid crystalline and surfactant properties, Csiba et al. [15] synthesized some amphiphilic derivatives of L-galactono-1,4-lactone 24, a by-product of the sugar beet industry available in large quantities. Reactions between 24 and hexyl, heptyl, octyl, decyl, dodecyl, and myristyl aldehydes on montmorillonite KSF or KIO were performed in a focused open-vessel micro-wave system for 10 min in the absence of solvent (Scheme 12.10). Protected derivatives 25a-f were afforded with yields (60-89%) considerably better than those (22-38%) obtained by conventional heating for 24 h in the presence of sulfuric acid. 

Treatment of the diamide 77 with dibutyltin dichloride affords the 2,2-bis(2-[4(/ ),5(5)-diphenyl-1,3-oxazolinyl])propane 78, while successive reaction of 77 with mesyl chloride and aqueous ethanolic sodium hydroxide yields the diastereomer 79 <96TI3649>. The (+)- and (-)-forms of the chiral oxazoline 80 were used as ligands for palladium catalysed allylic amination reactions thus the acetate 81 and benzylamine gave the optically active amine 82 in excellent enantiomeric excess <97JOC55Q8>. The enantioselective catalytic alkylation of aldehydes RCHO (R = n-heptyl, Ph, cyclohexyl or PhCH=CH) with allyluibutyltin in the presence of chiral bis(oxazolinyl)zinc complexes, c.g., 83, leads to alcohols 84 in 40 6% enantiomeric excess <97TL145>. 

Caspary (1968a) indicated the usefulness of low temperature for the identification of materials having room-temperature spectra which are similar to each other (e.g., -hexyl bromide and n-heptyl bromide -butylamine and n-hexylamine and sebacic acid di-n-butyl ester and azelaic acid di- -butyl ester [Fig. 3.16]). He compared other compounds at room temperature and low temperature, such as various ketones (19686) and aldehydes (1965). These substances, all of which are liquids at room temperature, show many differences at the low temperature. 

Synonyms Aldehyde Cl4 Aldehyde Cl4 pure y-Heptyl butyrolactone 5-Heptyldihydrofuran-2-one 4-Hydroxyundecanoic acid lactone 5-Hydroxyundecanoic acid y-lactone Peach aldehyde Undecanoic y-lactone Undecan-4-olide y-Undecyl lactone Classification Heterocyclic compd. nonaromatic lactone... 

Cyclohexylpropanol Diisobutyl ketone Isononyl aldehyde 2-Methyloctanal Nonanal 2-Nonanone cls-6-Nonen-1-ol trans-2-Nonen-1-ol Trimethylcyclohexanol C9H18O2 Amyl butyrate Amyl isobutyrate n-Butyl isovalerate N-Butyl-2-methylbutyrate Butyl valerate Ethyl heptanoate Heptyl acetate... 

Isobutyl heptyl ketone Laurie aldehyde Methyl nonyl acetaldehyde C12H24O2 Amyl heptanoate Butyl octanoate 2-Butyl octanoic acid Coconut acid Decyl acetate Dihydrocitronellyl acetate Dimethyloctanyl acetate Ethyl decanoate Hexyl hexanoate Isodecyl acetate Laurie acid Methyl undecanoate Octyl butyrate C12H24O2 V Cb Calcium laurate C12H24O2 xBa xCd Barium cadmium laurate C12H24O3... 

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