Patent GB-777515-A (GB)
Title: Improvements in or relating to tertiary alcohols
Inventor: NORMANT HENRY
IPC: C11B9/00
Filed: 1955-04-13
Abstract: The invention comprises diethylenic alcohols of the general formula <FORM:0777515/IV(b)/1> in which R1 and R2 each represent a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms or an aryl group, R3 is hydrogen or a methyl group, and R4, R5 and R6 each represent a hydrogen atom or an alkyl group containing from 1 to 5 carbon atoms, at least one of the symbols R4, R5 and R6 representing an alkyl group.  These alcohols and those in which all of the groups R4, R5 and R6 are hydrogen are obtained by condensing a g -ethylenic ketone of the general formula <FORM:0777515/IV(b)/2> with an ethylenic organo-magnesium derivative of the general formula <FORM:0777515/IV(b)/3> in which X is a halogen atom (preferably bromine) and then decomposing the complex formed with water. Preferably, the ethylene organo-magnesium derivative is employed in excess and the complex is decomposed with a cold aqueous solution of ammonium chloride.  The ethylenic organo-magnesium derivatives may be prepared by reacting magnesium with a solution, in tetrahydrofuran, of an ethylenic compound of the general formula <FORM:0777515/IV(b)/4> In the example, magnesium is introduced into dry tetrahydrofuran containing a trace of iodine and a solution of vinyl bromide in tetrahydrofuran is added; a solution of 2-methyl-hept-2-en-6-one in ether is added and the mixture is left to stand; a saturated aqueous solution of ammonium chloride is added to decompose the magnesium complex formed to give dl-linalool.  If instead of vinyl bromide, 1-bromopropene, 1 - bromo - hept - 1 - ene, 1 - bromoisobutene and 2-bromopropene are used, 2.6-dimethylnona - 2.7 - dien - 6 - ol, 2.6 - dimethyl - trideca-2.7 - dien - 6 - ol, 2.6.8 - trimethyl - nona - 2.7 - dien - 6 - ol and 2.6.7 - trimethyl - octa - 2.7 - dien-6-ol respectively are obtained.ALSO:New diethylenic alcohols of general formula <FORM:0777515/VI/1> in which R1 and R2 represent a hydrogen atom or an alkyl group containing 1-4 carbon atoms or an aryl group, R3 represents a hydrogen atom or a methyl group, and the symbols R4, R5 and R6 each represent a hydrogen atom or an alkyl group containing from 1 to 5 carbon atoms, one at least of the symbols R4, R5 and R6 representing an alleyl group, may be used in perfumes and toilet preparations. One or more of the alcohols may be mixed with a perfumery base material such as ethyl alcohol or a concentrated aqueous solution of ethyl alcohol, and the mixture may cntain such additives as gums, balsams and oleo-resins. Other perfumery base materials may take the form of cold creams, hand lotions, hand creams, vanishing creams, face powders, rouges, lipsticks, shampoos, hair oils and hair creams compounds from such waxes as beeswax or spermaceti, oils such as castor oil, mineral oils or lanolin, soaps, glycerin, surface active agents, gums, such as gum tragacanth, talc, chalk, kaolin, water repellants such as zinc stearate, pigments and dyes.  The perfumery base materials may also have as additives other odoriferous substances of synthetic or animal or vegetable origin in addition to one or more of the new alcohols.