Alcohols, applications

M. Adinolfi, G. Barone, A. Iadonisi, and M. Schiattarella, An easy approach for the acetylation of saccharidic alcohols. Applicability for regioselective protections, Tetrahedron Lett., 44 (2003) 4661 -663. 

Geoghegan, K.E, and Stroh, J.G. (1992) Site-directed conjugation of nonpeptide groups to peptides and proteins via periodate oxidation of a 2-amino alcohol. Applications to modification at N-terminal serine. Bioconjugate Chem. 3, 138-146. 

The hydrogenolysis of the thiol esters of carboxylic acids offers a delicate method for reducing an acid to the corresponding aldehyde or alcohol application of this method to the sugar series has been made by Wolfrom and Karabinos who reduced D-ribonyl chloride tetraacetate (LXXV) to aldehydo-D-ribose tetraacetate (LXXVII) in 22% yield via ethyl thiol-D-ribonate tetraacetate (LXXVI). The desulfurization of the thiol ester (LXXVI) was carried out with a somewhat aged sample of Raney nickel" which doubtless had less activity than the... 

C. Lamy, E. M. Belgsir, and J.-M. Leger, Electrocatalytic oxidation of aliphatic alcohols Application to the direct alcohol fuel cell (DAFC), J. Appl. Electrochem. 31, 799-809 (2001). 

The dermal adsorption of DEET in humans has been studied in the Netherlands by application of [14C] DEET as undiluted technical material or as 15% solutions in alcohol. Labeled material was recovered from the skin, and absorption of DEET was indicated by the appearance of label in urine after two hours of skin exposure. About 5—8% of the applied treatments was recovered as metabolites from urine, and excretion of metabolites in the urine came to an end four hours after exposure ended. DEET did not accumulate in the skin, and only a small (less than 0.08%) amount ended up in feces. Curiously, less has been absorbed through skin from 100% DEET application (3—8%, mean of 5.6%) than from 15% alcohol application (4—14%, mean of 8.4%). These results have been described as consistent with previous absorption/metabolism studies using guinea pigs, rats, and hairless dogs. Other publications on DEET toxicology have been cited (92). 

The first attempts to prepare cobalt and nickel ethoxides were reported in 1936 by Meerwein [1102] and Kandelaki [875]. Application ofNaOR in the exchange reactions could not, however lead to the obtaining of the pure products of purpose as they were insoluble in the parent alcohol. Application of LiOR for this purpose permitted Adams et al. in 1966 to obtain the individual M(OMe)2 — derivatives of id-transition elements in the series from Cr to Cu [6]. In the 1980s Mehrotra et al. have described the homologous series of Ni(OR)2 — from methoxide to r-hexyloxide [99], and also Co(OR)2, where R = Me,Et, Pr [1108]. On the alkoxylation of CoH(N2)(PPh3)3 by esters, phenol, or fluorinated ketones, Hayashi et al. [720] have obtained a series of tetrahedral [Co (OR)(PPh3)3] complexes. 

Gessner, P. K. Method for the assay of ethanol and other aliphatic alcohols applicable to tissue homogenates and possessing a sensitivity of 1 pg/ml. Anal. Biochem., 1970,... 

Deska J, Backvall J-E (2009) Enzymatic kinetic resolution of primary allenic alcohols. Application to the total synthesis and stereochemical assignment of striatisporolide A. Org Biomol Chem 7 3379-3381... 

Dijksman, A. Elzinga, M., J. Li, Yu-Xin, Arends, I., Sheldon, R., A. Efficient ruthenium-catalyzed racemization of secondary alcohols application to dynamic kinetic resolution. Tetrahedron Asymmetry 2002, 13, 879-884. 

Lotions (aqueous-alcoholic) Application + d May need solubilizers in low-alcoholic formulations... 

Dahlen, A, Sundgren, A, Lahmann, M, Oscarson, S, Hilmersson, G, Sml2/water/amine mediates cleavage of allyl ether protected alcohols — application in carbohydrate synthesis and mechanistic considerations, Org. Lett, 5, 4058-4088, 2003. 

Manufacturing process Several methods exist for reduction of o-anisic aldehyde to o-anisic alcohol, however, direct reduction by hydrogen using Raney-Nickel catalyst system at 90-100° C and 5-7 atm pressure has been commercially most attractive. Most of the key players of p-anisic alcohol such as BASF, Givaudan, Koffoeks, etc. also produce some quantities of o-anisyl alcohol. Application areas include flavor and fragrance, pharmaceuticals, etc. Global demand has been estimated at 300-350 tpa. 

Young, J-j., Jung, L-j., and Cheng, K-m., 2000, AmberIyst-15-calalyzed Sn2 oxaspirocyclization of secondary allylic alcohols. Application to the total synthesis of spirocyclic ethers Iheaspiiane and theaspirone. 

Furan resins. Thermosets manufactured from furan derivatives such as furfural, furfuryl alcohol, tetrahydrofurfuryl alcohol. Applications foundry resins and core binders, acid-proof coatings, putties. 

Krishnan S, Bagdanoff JT, Ebner DC, Ramtohul YK, Tambar UK, Stoltz BM (2008) Pd-Catalyzed Enantioselective Aerobic Oxidation of Secondary Alcohols Applications to the Total Synthesis of Alkaloids. J Am Chem Soc. 130 13745... 

W. (1996) Catalytic racemisation of alcohols applications to enzymatic resolution reactions. Tetrahedron Lett., 37 (42), 7623-7626. 

Ester Carboxylic acid Alcohol Application References... 

Method for the Assay of Ethanol and Other Aliphatic Alcohols Applicable to Tissue Homogenates and Possessing a Sensitivity of 1 Microgram/ml. 

Lamy C, Belgsir EM, LegCT JM (2001) Electro-catalytic oxidation of aliphatic alcohols application... 

FIGURE 5.2 A scanning electron microphotograph of a MEA (left), and a PTL/MPL assembly (right). The thick membrane and electrodes in the MEA are typical of direct alcohol applications. The structural differences between the GDL and PTL are clearly visible on the right. (From Fraunhofer Institute for Solar Energy Systems. With permission.)... 

Lo, L. Liao, Y Kuo, C. Chen, C. A novel coumarin-type derivatizing reagent of alcohols Application in the CD exciton chirality method for microscale structural determination. Org. Lett. 2000, 2,683-685. 

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