6-Methyl-3-octanol

This method has been applied to the synthesis of (S)-2-methyl-4-octanol, an aggregation pheromone of Metamasius hemipterus.56... 

The chiral alcohol, 2-methyl-4-octanol, was identified as an aggregation pheromone from airborne volatiles produced by male and females of the sugarcane weevil Sphenophorus levis. Enantiomeric resolution by GC with a chiral column showed that the natural alcohol possessed the S configuration. The alcohol elicited aggregation behavior among adults. ... 

R) and (S)-3-octanol, (i )-2-dodecanol, (i )-2-methyl-4-heptanol and (i )-2-methyl-4-octanol, the pheromones of Myrmica scabrinodis, Crematogaster castanea, C. liengmei, C. auberti and Metamasius hemipterus were synthesized starting from nonracemic P-hydroxy sulfides. 

Zarbin, P. H. G. Princival, J. L. dos Santos, A. A. de Oliveira, A. R. M. Synthesis of (S)-( + )-2-Methyl-4-octanol Male-Specific Compound Released by Sugarcane Weevil Sphenophorus levis. Journal of the Brazilian Chemical Society. 15 (2004) 331-334. 

Alkali Fusion. Tha alkaU fusion of castor oil using sodium or potassium hydroxide in the presence of catalysts to spHt the ricinoleate molecule, results in two different products depending on reaction conditions (37,38). At lower (180—200°C) reaction temperatures using one mole of alkah, methylhexyl ketone and 10-hydroxydecanoic acid are prepared. The 10-hydroxydecanoic acid is formed in good yield when either castor oil or methyl ricinoleate [141-24-2] is fused in the presence of a high boiling unhindered primary or secondary alcohol such as 1- or 2-octanol. An increase to two moles of alkali/mole ricinoleate and a temperature of 250—275°C produces capryl alcohol [123-96-6] CgH gO, and sebacic acid [111-20-6] C QH gO, (39—41). Sebacic acid is used in the manufacture of nylon-6,10. 

Some alcohols that have been converted into the corresponding fluorides by reactions with diethyldminosulfur trifluoride include 1-octanol, 2-methyl-2-butanol, isobutyl alcohol, cyclooctanol, ethylene glycol, crotyl alcohol, 2-phenylethanol, 2-bromoethanol, ethyl lactate, and ethyl a-hydrox3maphthaleneacetate. ... 

Thus, in the series of Ti measurements of 2-octanol (42, Fig. 2.27) for the methyl group at the hydrophobic end of the molecule, the signal intensity passes through zero at Tq = 3.8 s. From this, using equation 10, a spin-lattice relaxation time of Ti = 5.5 s can be calculated. A complete relaxation of this methyl C atom requires about five times longer (more than 30 s) than is shown in the last experiment of the series (Fig. 2.27) Tj itself is the time constant for an exponential increase, in other words, after T/ the difference between the observed signal intensity and its final value is still 1/e of the final amplitude. 

Figure 15.11 (a) Total ion clnomatogram of a Grob test mixture obtained on an Rtx-1701 column, and (b) re-injection of the entire clnomatogram on to an Rtx-5 column. Peak identification is as follows a, 2,3-butanediol b, decane c, undecane d, 1-octanol e, nonanal f, 2,6-dimethylphenol g, 2-ethylhexanoic acid h, 2,6-dimethylaniline i, decanoic acid methyl ester ], dicyclohexylamine k, undecanoic acid, methyl ester 1, dodecanoic acid, methyl ester. Adapted from Journal of High Resolution Chromatography, 21, M. J. Tomlinson and C. L. Wilkins, Evaluation of a semi-automated multidimensional gas chromatography-infrared-mass specti ometry system for initant analysis , pp. 347-354, 1998, with permission from Wiley-VCH. 

Properties Methyl iso-butyl ketone (MIBK) Tributyl phosphate (TBP) 2-octanol... 

Benzenesulfomc acid, 4-methyl, 2,2 dimeth ylpropyl ester [1-Propanol, 2,2-di-methyh, p-toluenesulfonate], 55, 112 Benzenesulfomc acid, 4-methyl-, esters [p-Toluenesulfonates], reaction with organocuprates, 55, 112 Benzenesultonic acid, 4-methyl-, ( )-4-hexen-l-yl ester ]( )-4-Hexen-l-yl p-toluenesulfonate], 55, 57 Benzenesulfomc acid, 4-methyl-, 1-methyl-heptyl ester [2-Octanol, p-toluenesulfonate], 55,112... 

Benzenesulfomc acid 4 methyl, octyl ester [1-Octanol, p-toluenesulfonate], 55, 112... 

Analog lassen sich Carbonsaure-ester mit 1,5- Mol-Aquiv. Natriumboranat in Gegenwart von 1 Mol-Aquiv. Benzanilid in 2-Methyl-pyridin bei 100°in 5-6 Stdn. zu Alkoholen reduzieren" [z.B. Herstellungvon Octanol (74% d.Th.), Nonanol (87% d.Th.) und 4-Cyano-benzylalkohol (89% d.Th.)]. 

K(,(., calculated from the octanol-water coefficient (K w) solubility, and melting point data ranged from 2.93 to 3.47, and compared favorably with literature values (Karickhoff 1981). McLean et al. (1988) estimated a lower Kq . of 39, equal to a log of 1.59. More recently, a of 5,100, equal to log 3.7, has been reported (HSDB 1999). These values indicate that methyl parathion is moderately mobile to immobile in soil (Swann et al. 1983). 

Under microwave irradiation and applying MCM-41-immobilized nano-iron oxide higher activity is observed [148]. In this case also, primary aliphatic alcohols could be oxidized. The TON for the selective oxidation of 1-octanol to 1-octanal reached to 46 with 99% selectivity. Hou and coworkers reported in 2006 an iron coordination polymer [Fe(fcz)2Cl2]-2CH30H with fez = l-(2,4-difluorophenyl)-l,l-bis[(l//-l,2,4-triazol-l-yl)methyl]ethanol which catalyzed the oxidation of benzyl alcohol to benzaldehyde with hydrogen peroxide as oxidant in 87% yield and up to 100% selectivity [149]. An alternative approach is based on the use of heteropoly acids, whereby the incorporation of vanadium and iron into a molybdo-phosphoric acid catalyst led to high yields for the oxidation of various alcohols (up to 94%) with molecular oxygen [150]. 

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