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Tschugaeff (Chem. Centralbtatt. 1905 i , p 94) obtains pure d-borneol as follows.—Impure d-borneol (containing isoborneol) obtained in the reduction of camphor is dissolved in See also:

XYLENE, or DIMETHYL BENZENE, C6H4(CH3)2

xylene and converted into the sodium See also:

salt by metallic sodium. This salt is then turned into the xanthate, CIOH17OCS2Na, which with methyl sulphate yields the corresponding methyl ester. The unchanged isoborneol is removed by See also:

steam See also:

DISTILLATION (from the Lat. distillare, more correctly destillare, to drop or trickle down)

distillation, which also decomposes any methyl. xanthate of isoborneol that may have been formed. The See also:

RESIDUE (through the French, from the Lat. residuum, a remainder, from residere, to remain)

residue is crystallized and hydrolysed, when pure borneol is obtained. It behaves as a secondary alcohol. Nitric See also:

ACID (from the Lat. root ac-, sharp; acere, to be sour)

acid oxidizes it to camphor and when heated with See also:

POTASSIUM [symbol K (from kalium), atomic weight 39.114 0=16)]

potassium bisulphate, it gives camphene. With See also:

PHOSPHORUS (Gr. 4ws, light, sPEpety, to bear)

phosphorus pentachloride it forms a bornyl chloride, identical with pinene hydrochloride. Isoborneol is a See also:

TERTIARY

tertiary alcohol which may be obtained by dissolving camphene in glacial acetic acid, adding dilute sulphuric acid and heating to 50-6o° C. fcr a few minutes, the isobornyl acetate so formed being then hydrolysed (J. Bertram and H. Walbaum, loc. cit.).

It crystallizes in leaflets, which readily See also:

SUBLIME (Lat. sublimis, exalted)

sublime. Chromic acid oxidizes it to camphor. Thujone (tanacetone), C10H18O, is found in many essential oils. Oil of thuja contains chiefly a-thujone, and oil of tansy chiefly ,B-thujone. Oil of See also:

artemisia and oil of See also:

SAGE, RUSSELL (1816-1906)

sage contain a mixture of the two, whilst oil of See also:

ABSINTHE

absinthe contains principally the )3-variety. The two forms may be obtained by fractional distillation of the oils, followed by a fractional, See also:

CRYSTALLIZATION

crystallization of their semicarbazones from methyl alcohol. a-Thujone is laevo-rotatory and when warmed with alcoholic potash it is partially converted into /3-thujone. Sodium in the presence of alcohol reduces it to thujyl alcohol, which on re-oxidation is converted into l-thujone. The fl-See also:

FORM (Lat. forma)

form is dextro-rotatory and is partially converted into the a-variety by alcoholic potash. When heated to 28o° thujone is transformed into the isomeric carvotanacetone (A6-terpenone-2). On boiling with ferric chloride it yields See also:

CARVACROL, or CYMOPHENOL

carvacrol. Hot dilute sulphuric acid converts it into isothujone (dimethyl-i . 2-isopropyl-3-cyclopentene-I-one-5).

Thujone behaves as a saturated See also:

compound and forms a characteristic tribromide. When heated with See also:

ZINC

zinc chloride it yields hydropseudocumene. According to F. W. Semmler (See also:

BEE (Sanskrit blza, AS. ben, Lat. apis)

Bee., 1900, 33, p. 275; 1903, 36, p. 4367) it is to be considered as a methyl-2-isopropyl-5-bicyclo-(o . I • 3)-hexanone-3. Carone, C1oH160, is a trimethyl-3 . 7 • 7-bicyclo-(o . I • 4)-heptanone-2, obtained by acting with alcoholic potash on dihydrocarvone hydrobromide (A. v. See also:

BAEYER, JOHANN FRIEDRICH WILHELM ADOLF VON (1835– )

Baeyer, Ber., 1896, 29, pp.

5, 2796; 1898, 31, pp. 1401, 2067). It Is a colourless oil, having the odour of camphor and See also:

PEPPERMINT

peppermint, and boiling at 210° C. It is known in d-, l-, and i-forms. It does not combine with sodium bisulphite. When heated it is transformed into carvenone. It is See also:

STABLE

stable to See also:

COLD (in O. Eng. cald and ceald, a word coming ultimately from a root cognate with the Lat. gelu, gelidus, and common in the Teutonic languages, which usually have two distinct forms for the substantive and the adjective, cf. Ger. Kolte, kalt, Dutch koude

cold potassium permanganate See also:

SOLUTION (from Lat. solvere, to loosen, dissolve)

solution, but on heating gives a dibasic acid, caronic acid, C5H8(See also:

CO2H

CO2H)2, which Baeyer suggested was a See also:

gem-dimethyltrimethylene-r • 2-dicarboxylic acid. This was confirmed by W. H. See also:

PERKIN, SIR WILLIAM HENRY (1838-1907)

Perkin, junr. (Jour. Chem.

See also:

Soc., 1899, 75, p. 48) who synthesized the acid from dimethylacylic See also:

ETHYL

ethyl ester. This ester with ethyl malonate yields ethyldimethylpropanetricarboxylic ester, which on See also:

HYDROLYSIS (Gr. 6Swp, water, Anew, to loosen)

hydrolysis and subsequent heating is converted into t913-dimethyl glutaric acid. The a-bromdirrethyl ester of this acid when heated with alcoholic potash yields cis-, and trans-caronic acids. Eucarvone, C1oH1,O, is a trimethyl-3.7.7-bicyclo-(0•I.4)-heptene-3-one-2. O. Wallach (Ann., 1905, 339, p. 94) suggests that the ketone possesses the structure of a trimethyl-r .4 • 4-cycloheptadiene-5 . 7-one-2. Phosphorus pentachloride converts it into 2-chlorcymene (A. Klages, Ber., 1899, 32, p. 2558).

Camphor, C1oH16O, is a trimethyl-r . 7 . 7-bicyclo-(I • 2 • 2)-heptanone-2. The d-variety is found in the camphor See also:

tree (Laurus camphora), from which it may be obtained by distillation in steam. The l-variety is found in the oil of Matricaria parthenium. It crystallizes in transparent prisms which possess a characteristic odour, sublimes readily and is easily soluble in the usual organic solvents. It boils at 209° C. and melts at 176° C. (circa). The d-form may also be obtained by the distillation of See also:

CALCIUM [symbol Ca, atomic weight 40.0 (o= x6)]

calcium homocamphorate (A. See also:

Haller, See also:

Bull. Soc. Chim., 1896 (3), 15, p.

324). When heated with phosphorus pentoxide it yields cymene, and with See also:

IODINE (symbol I, atomic weight '26.92)

iodine, carvacrol. Nitric acid oxidizes it to camphoric acid, C8H14(CO2H)2, camphoronic acid, C9H1306, and other products. It forms an oxime with See also:

HYDROXYLAMINE, NH2OH

hydroxylamine which on dehydration yields a nitrile, from which by hydrolysis carnpholenic acid, C9HISCO2H, is obtained It combines with See also:

ALDEHYDES

aldehydes to form alkylidene compounds, and yields oxymethylene compounds when subjected to the " Claisen " reaction. It does not combine with the alkaline bisulphites. It is readily substituted by See also:

CHLORINE (symbol Cl, atomic weight 35`46 (0=16)

chlorine and See also:

BROMINE (symbol Br, atomic weight 79-96)

bromine; and with fuming sulphuric acid forms a camphor sulphonic acid. Sodium reduces it, in alcoholic solution, to borneol. When heated with sodium formate to 12o° C. it is converted into bornylamine. See also:

Caro's acid converts it into campholid, and a compound C10H1E0, (A. v. Baeyer and V. Villiger, Ber., 1899, 32, p. 3630).

When heated with concentrated sulphuric acid to 105-110° C. it yields carvenone and 4-aceto-r • 2-xylol (J. Bredt, Ann., 1901, 314, P. 371).

End of Article: ALCOHOL AND KETONE

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