DE1964405A1 - Alk-1-en-6-ols - Google Patents

Description

Badische Anilin- & Soda-Fabrik AG 1 9644 OS

Our sign 0, Z ₀ 26 537 Mi / Fe 6700 Ludwigshafen, December 22, 1969

Alk-1-en-6-ols

The present invention relates to alk-1-en-6-ols in general Formula I.

t? 4 OH _π 5

R -GH - "" CHp I.

■ it II ^

* Ή) GH ₂ ^ G

"" ■ * "- GH R ¹

'2

14. ·· 2 3

in which R and R are methyl or ethyl groups, R and R are water

substance or methyl groups and R is hydrogen or an alkyl group with 1 to 6 0 atoms.

It has been found that these compounds are more well known Way, if you get an alk-1-en-6-one of the general Formula II

R ³ -OH GH ₂

uHr> ^ G JI

EAR'

with an organometallic compound M - R, in which M a

Alkali metal or the alkaline earth metal halogen radical anεκ
G-rignard compound means, and R ^ is one of the defined alkyl groups or, if R Waaseratoff implies, that the carbonyl group is reduced to the hydroxyl group.

The starting compounds II are known or can be obtained by known methods, e.g. B. by reacting alkenylcatones R ^ -GQ- GR ⁵ = GH ₂ with olefins R ² O - GR - OH-, 2-Methylhept-i- is of particular importance among the compounds II

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BAD ORKSJNAl

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eri-6-one, 2-ethylhept-1-en-6-one, 2,3-dimethylhept-1-en-6-one, the 2 ^ -Dimethylhept-i-en-e-one and the 2-Methyloct-1-ΘΠ-6-0Π.

Among the organometallic compounds M-R are the Grignard compounds of the type R - MgGl are preferred for economic reasons. With regard to the properties of the process products Methyl and ethyl magnesium chloride are special important - the implementation of the organometallic compounds

5
dung MR with II is carried out according to the generally accepted methods, so that there is no need for further explanations. The same applies to the case RH, for the reduction of the ketones II to the corresponding alcohols, which can be carried out, for example, with sodium boronate, and for the isolation and purification of the compounds L

The alk-1-en-6-ols according to the invention are characterized by novel and characteristic fragrance and can be found in this property for a wide variety of purposes in dec perfumery and cosmetics and for odor improvement / of industrial products such as washing powders, glues, Ki.nuii; atomic dispersions and the like use. The substances I generally have have a llnalool-like odor are compared to sum Linalool, however, is more resistant to acids and alkalis, so that they are particularly suitable for perfuming soaps and other detergents.

example 1
2,6-dimethylhept-1-en-b-ol

A solution prepared in the usual way of 89.5 g of 0.2 mol) methylnagneTiunKihlorid and 500 ml of tetranydrofuran is ^{gradually added at 20 0} O with 126 g (1 mol) of 2-methylhept-1-en-6 -on and then the reaction mixture works in a likewise known manner on the 2, b-dimethylhept-1-en-6-ol to »The yield of pure product is 91 $ \ Kp = s 40 to 45 ° ö / 0,? Torr ; ujp = 1, -4427.

The connection smells like bergamot with a minnish note,

109827/1931 -3-

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Examples 2 "to 4

In the manner indicated in Example 1, one obtains

2.) from 2,3 - dimethylhept-1 - en-6-one and methylmagne siumclilorid 2,3,6-trimethylhept-1-en-6-one; Yield 90%; Bp = 87 to 89 ° 0/19 torr; njp = 1.44565 Fragrance note: Linalool-like but with a gampfer note »

3.) 2,6-Dimethyloct-1-en-6-ol from 2-methylhept-1-en-6-one and ethylmagnesium bromide; Yield 75 1 ° \ Kp = 86 ⁰ C / 11 Torr; n ^ = 1.4473; Fragrance note: lilac-like.

4 «) 2,6,7-trimethyloct-1-en-6-ol from 2-methylhept-1-en-6-one and isopropylmagnesium bromide; Yield 55 I> \ Kp = 97 to 98 ° C / 12 Torr; ηψ = 1.4502; Fragrance note: fruity towards peach, apricot.

Example 5
6-methylhept-ö-en-2-ol

Mau added 10 g of sodium borate to a solution of 126 g of 6-methylhept-6-en-2-one and 250 ml of ethanol in portions at room temperature, allowed the mixture to react for a further 5 hours and then worked it up on the Yerfahrena product as usual. The yield is $ 76; Bp = B9 to 91 ° O / 22 torr; n ^ ⁵ = 1.4422.
Fragrance note: linalool-like with a green note.

1Ü9B27 / 193 1 -4-

r ORIGINAL BATHROOM.

Claims (7)

O.Z. Claims Alk-1-en-6-ols of the general formula R ⁵ -GH O t ti CH ₉ / C ^ -GH R to R ^ in which R and R are methyl or ethyl groups, R and R are water substance or methyl groups and R is hydrogen or an alkyl group with 1 "to 6 G-atoms" mean. 2. 2,6-Eimethylhept-1-en-6-ol. 3. 2,3,6-Trimethylhept-1-en-6-ol. 4. 2,6-Dimethyloct-1-en-6-ol. 5. 2,6,7-Trimethyloot-1-en-6-ol. 6. 2-methyl-hept-1-en-6-ol. 7. A process for the preparation of the alk-1-en-6-ols according to Claim 1, characterized in that an alk-1-en-6-one of the general formula II R ⁴ R ³ -GH GH ₀ GH ₂ G ^^ GH ^ "R ¹ gate with an organometallic compound M - R, in which M is an alkali metal or the alkaline earth metal halogen radical of a Grignard muzzle means, and R a definition according to the definition Is an alkyl group, or, if R ^ is hydrogen, that the carbonyl group is reduced to the hydroxyl group, Badi30he Anilin- & Soda-Fabrik AG 109827/1931 BAD ORtGlNAl.