JPS6031812B2 - Hydroxy-aldehyde - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel hydroxyaldehydes of interest as aroma chemicals and processes for their preparation.

The novel hydroxyaldehydes according to the invention are 4,8-
It is dimethylnonane-8-all-R, and is represented by the following formula. This novel compound is prepared by hydrogen and carbon monoxide in the presence of a rhodium or cobalt compound, preferably a rhodium or cobalt carbonyl derivative, as a catalyst.
, 7-dimethyl-1-octen-7-ol (3,7-dimethyl Ct-en-7101).

Particularly suitable rhodium carbonyl derivatives are those which contain, in addition to one or more carbonyl groups, one hydride group and/or one or more vicinal containing ligands. The catalyst is the compound HRh(CO)(P(C6day5
)3)3 or C02(CO)8, or heterogeneous catalysts obtained, for example, by incorporating such compounds on a solid support such as silica. The hydroformylation temperature is preferably between 500 and 200 qo and the pressure is preferably below 150 bar. This process may be carried out in an organic solvent such as an aromatic hydrocarbon such as benzene. The hydroxyaldehydes of the present invention are of interest as aroma chemicals.

The odor of this compound can be said to be a characteristic fresh flower-like odor similar to that of mugette. In some respects it resembles the known compound hydroxy-citronellal (3,7-dimethyloctan-7-ol-1-al). However, the odor of the compounds of the present invention is much milder and does not exhibit the pungent odor always associated with hydroxy-citronellal. Furthermore, it is superior to hydroxycitronellal in terms of retention and diffusivity. It is generally accepted in the fragrance industry that even though there is a chemical relationship, such as that between the compounds of the present invention and the known lower homologue hydroxy-citronellal,
It is thought that the evocative nature of the former cannot be predicted from the latter.

However, one skilled in the art would expect that the chemical properties of both compounds, such as their stability in different media, would be approximately the same.O Surprisingly, the compounds of the present invention are more effective than hydroxycitronellal, especially for surface cleaning. It has been found to be even more stable in alkaline media such as detergents and detergents.

The compounds of the invention can be used as fragrance materials as such, or they may be combined with other single compounds or mixtures (eg essential oils) to form fragrance compositions.

The term "fragrance composition" means a mixture of fragrance materials and auxiliary materials, optionally dissolved in a suitable solvent or mixed with a suitable powder base, and used to impart a desired odor to various products.

Examples of such products include soaps, cleaning products, disinfectants, and room deodorizers. The amount of compounds used according to the invention can vary widely depending on the desired odor effect. It is preferred to use 0.1% by weight or more in concentrated fragrance compositions. Of course, these amounts may be reduced proportionately by dilution or by application to the product to be aromatized. Next, an example will be used.

Example 1 3,7-dimethyl-1-octen-7-ol (i8.0), tris(triphenylphosphine)hydride carbonylrhodium(1) (0.20) in a 100mm stainless steel autoclave fitted with an electromagnetic pestle
2) and benzene (20 cm) were added.

The autoclave was pressurized to 85 degrees using an equal volume mixture of hydrogen and carbon monoxide. Next, add this to 100
It was kept for 2 hours. After cooling to 2,000 ℃ and reducing the pressure, the contents of the autoclave were fractionally distilled in vacuo to a boiling point of 0.
8 Skin Hg 10? -106 qo of aldehyde product (15.4 pm) was obtained.

The product could be purified by spinning band distillation to the desired aldehyde 4,8-dimethylnonene-8-ol-1. The HMR spectrum of this compound was measured in deuterochloroform solution at 6 Senmachi z in reference to a tetramethylsilane standard, and the absorption was as follows.

6 = 9.81 leg plate (triple line, CHO) 6 = 2.42 wind (two triple lines, 8 = 2.0 respect (single line, OH) 6 = 1.21 leg plate (single line, (CH3) 2C) 6=0.8
&Blood(CH3CH)6=1.0-1. Yufu (9H) The product had a fresh floral, mugwet-like odor.

Example 2 A maguette type fragrance composition was obtained according to the following recipe (
Amounts are in parts by weight).

4,8-dimethylnonan-8-ol-1-al
350 citronellol 200 linalool
100 citronellyl acetate 30 pendyl acetate
20 terpineol
30 linalyl acetate
503-(p-tert-butylphenyl)-
2-methylpropanal
20 phenylethyl alcohol 50
Alpha-hexyl cinnamaldehyde 203-phenylprobenol 10 indole
1) 20 alpha ionone
1) 50 Dupical
1) 2) 30 ethyl linary acetaldehyde acetal ・) 3) 10
Cis-3-hexen-1-yl acetate 1) 10% diethyl phthalate solution 2) NaardenInterMtionaIN. V
．． Commercially available aroma compounds 3) British Patent No. 1371727

Claims (1)

Claims: 1. 4,8-dimethylnonan-8-ol-al, which is a hydroxy-aldehyde. 2 In the preparation of 4,8-dimethylnonan-8-ol-1-al, a hydroxy-aldehyde, 3,7-dimethyl-1-octene is reacted with hydrogen and carbon monoxide in the presence of a rhodium or cobalt compound as a catalyst. -7
- A production method characterized by hydroformylating ol. 3. The production method according to claim 2, wherein the catalyst is rhodium or a cobalt carbonyl derivative. 4 The catalyst is HRh(CO)(P(C_6H_5)_3)
The manufacturing method according to claim 3, which is _3. 5. Process according to any of claims 2-4, wherein the temperature is 50°-200°C and the pressure is 150 bar or less. 6. The production method according to any one of claims 2 to 5, wherein the hydroformylation is carried out in an aromatic hydrocarbon as a solvent. 7 Aromatic compositions or aromatized products containing 4,8-dimethylnonan-8-ol-1-al.