US 3,948,814 AGrant
Acetaldehyde Ethyl Linalyl Acetal Perfume Compositions
Issue Date:1976-04-06
•2 Claims
Abstract
Odorous acetaldehyde ethyl linalyl acetal, perfume compositions, materials or products comprising conventional constituents such as solvents, diluents and adjuvants and containing as an essential ingredient acetaldehyde ethyl linalyl acetal. Also the method of preparing perfume compositions by adding the acetal thereto and the method of preparing the acetal by reacting a solution of sulfuric acid in linalool to vinylethyl ether, adding soda thereto, separating and fractionating an organic layer with soda.
Metadata
Assignee
- Naarden International, N.V.
Inventor
- David de Rijke
Application Information
Application Number:US 2792974
Filing Date:1972-08-10
Priority Date:1971-08-11
Art Unit:125
Classifications
IPC:
A61K 746C07C 4330
Field of Search:
252260522615 A
Patent Drawings
This patent does not have any drawings.
Description
The invention relates to a process for the preparation of perfume compositions and perfumed products, which contain in addition to conventional constituents usual for this purpose an odorous component acetaldehyde ethyl linalyl acetal of the formula: ##SPC1##
Acetaldehyde ethyl linalyl acetal is a novel commpound not previously described in the literature. Acetaldehyde butyl linalyl acetal, an analogous compound has been described in Zh. Obshch. Khim. 16 (1946) 937-951 (Chem. Abstr. 41 (1947) 1999c) and in Sin. Org. Soedin 2 (1952) 154-161 (Chem. Abstr. 48 (1954) 569c), but without mention of odorous properties, if any. Acetaldehyde ethyl linalyl acetal acts as an intermediate product in the synthesis of 5.9-dimethyl-4.8-decadiene-1-al even though it has not been mentioned particularly and has not been isolated. (see Helv. Chim. Acta 50 (1967) 2095-2100 and the German "Auslegeschrift" 1,193,490, example 15).
This aldehyde is formed by rearrangement from acetaldehyde ethyl linalyl acetal and has a fatty, somewhat fruity odor, reminiscent of lauryl and tetradecylaldehyde.
It surprisingly now has been found that acetaldehyde ethyl linalyl acetal has an exalting flower odor, related to the odor of hydroxy citronellal. Thus, this acetal is very suitable for perfume compositions having a flower odor like rose, freesia and lily of the valley, as well as for giving a flowerlike undertone to other compositions. The acetal may be employed in quantities of from 10-15 percent by weight of the composition. However, the quantity may be varied dependent upon the perfumer and the ultimate aroma desired.
The preparation of acetaldehyde ethyl linalyl acetal can be carried out by the addition of linalool to vinylethyl ether (see German Auslegeschrift No. 1,193,490 and Zh. Obshch. Khim 16 (1946) 937-951). The following Example illustrates the preparation of acetaldehyde ethyl linalyl acetal.
Example I
Into an 1 l reaction flask is placed 216 g vinylethyl ether. Under stirring a solution of 0.2 g concentrated sulfuric acid (s.g. 1.84) in 154 g linalool is added over a 2 hour period at 30.degree.C. Then 100 g of a 10-percent soda solution are added to the reaction mixture and the entire mixture is stirred for half an hour. The organic upper layer is separated and fractionated with 0.5 g soda to obtain 186 g acetaldehyde ethyl linalyl acetal. The acetal has a boiling point of 90.degree.-94.degree.C. at 2 mm Hg; n.sub.D.sup.20 1,4495-1,4485. The addition of soda to the product to be distilled prevents the formation of 5.9-dimethyl-4.8-decadien-1-al during the fractionation.
The following Examples illustrate perfume compositions prepared according to this invention using the acetaldehyde ethyl linalyl acetal of Example I.
Claims
What I claim is:
1. A perfume composition comprising a mixture of perfumery materials including acetaldehyde ethyl linalyl acetal in an amount sufficient to give a flowerlike undertone to said composition.
2. The perfume composition of claim 1 containing from 10-15 percent by weight of acetaldehyde ethyl linalyl acetal.
Patent Citations (1)
| Patent | Date | Inventor | Cited By |
|---|---|---|---|
| DT821,203 | 1951-11-01 |
Non-Patent Literature (3)
- Shostakovskii, Chem. Abs., Vol. 41, 1947, p. 1999c.
- Keller, Chem. Abs., Vol. 55, 1961, p. 19983e.
- Moncrieft, The Chem. of Perf. Mat. United Trade Press, London, 1949, pp. 314-315.