Indane aldehydes and derivatives

Details Indane aldehydes and derivatives Indane aldehydes and derivatives

2001-01-26

2002-01-29

Hardee, John (Department: 1751)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C568S440000, C568S659000

Reexamination Certificate

active

06342612

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to new chemical entities and the incorporation and use of the new chemical entities as fragrance chemicals.
BACKGROUND OF THE INVENTION
There is an ongoing need in the fragrance industry to provide new chemicals to give perfumers and other persons ability to create new fragrances for perfumes, colognes and personal care products.
Indancarbaldehyde and Indan-2-yl-carbaldehyde are known in the art. They are reported to be made by hydroformylation of indene. It is taught that the ratio of the two product isomers can be controlled by varying reaction temperature and catalyst (U.S. Pat. Nos. DE 2,053,736 and DE 2,132,414). It is also disclosed that indancarbaldehyde can be converted using standard chemical techniques to the corresponding alcohol and acetate (Doyle, Michael M.; Jackson, Roy W; Perlmutter, Patrick, Tetrahedron Lett, 1989, 5357-5360), as well as the corresponding dimethylacetal (Corner, Avelino; Clement, Maria J.; Carcia, Hermenegildo; Primp, Jaime, Appl. Catal. 1990, 59(2),33-40).
These materials as well as other derivatives of indancarbaldehyde and indan-2-yl-carbaldehyde have not been used in the fragrance industry or reported to show utility as aroma chemicals or fragrance enhancers. There is an ongoing need for the creation of new aroma chemicals that impart floral, fruity and woody “notes” or aromas to enhance fragrance formulations.
SUMMARY OF THE INVENTION
The present invention provides novel chemicals, and incorporation of these chemicals to provide a fragrance for perfumes, toilet waters, colognes, personal products and the like. In addition, the present invention is directed to the use of related chemicals to enhance fragrance in perfumes, toilet waters, colognes, personal products and the like.
More specifically, the present invention is directed to new compounds of the formulae:
which can be represented by
where Z is selected from the group consisting of:
 where R=H or methyl.
Another embodiment of the invention is a method for enhancing a perfume by incorporating an olfactory acceptable amount of compounds of the formula:
where A is selected from the group selected consisting of:
where R is H or methyl
and Y is selected from the group consisting of H, CH
3
, C
2
H
5
, and C
3
H
7
.
These and other embodiments of the present invention will be apparent by reading the following specification.
DETAILED DESCRIPTION OF THE INVENTION
The present invention is directed to the following novel chemicals of the structures, the processes for synthesizing these novel materials, and their use in perfume formulation:
where the Z or Z
1
element is shown below.
IUPAC Name
Z element
2-indanyl-4-methyl-1,3-dioxolane

2-indanyl-1,3-dioxolane

3-indanyl-2-methylpropanal

1-(indanylmethoxy)prop-2-ene

1(indanylmethoxy)-2-methylprop-2-ene

Z
1
element
2-indan-2-yl-4-methyl-1,3-dioxolane

2-indan-2-yl-1,3-dioxolane

3-indan-2-yl-2-methylpropanal

1-(indan-2-yl-methoxy)prop-2-ene

1-(indan-2-yl-methoxy)-2-methylprop-2-ene
In addition to the compounds listed above, the present invention is directed to the use of the following compounds in fragrance formulations. These have the structures:
The Z and Z
1
element are as shown below:
IUPAC name
Z element
—CHO
Indancarbaldehyde

Indandimethoxymethane

Indanmethyl acetate

Indanmethyl propionate

Indanmethanol

Indanylmethylbutonate

Z
1
element
—CHO
Indan-2-carbaldehyde

Indan-2-yl-dimethoxymethane

Indan-2-yl-methylacetate

Indan-2-yl-methylpropionate

Indan-2-yl-methanol

Indan-2-yl-methylbutonate
The positional isomers of each derivative may be used separately, or preferably as a mixture derived from indancarbaldehyde and indan-2-yl-carbaldehyde, formed in a ratio of 60/40 to 90/10. Those skilled in the art will appreciate that the corresponding isomer ratio of the specified derivative will be formed in a corresponding ratio.
The novel compounds of the present invention are prepared by the following reactions:
1. Dioxolane derivatives:
where R=H
1
methyl, or ethyl
In this reaction, the indancarbaldehyde isomers are reacted with a glycol, such as propylene glycol or ethylene glycol, in an inert solvent such as toluene, while being heated at reflux. An acid catalyst is employed to help catalyze the reaction. Water is removed via azeotropic distillation to drive the reaction to completion.
2. Condensation reactions:
The mixture of indancarbaldehyde and indan-2-yl-carbaldehyde is reacted with aldehydes (wherein R=methyl, ethyl, propyl, isopropyl) in the presence of an alkali hydroxide (M=sodium, lithium, or potassium) in an alcoholic solvent (methanol, ethanol, isopropanol) to form the unsaturated carbonyl compound II. Carbonyl compound II may be reduced by catalytic hydrogenation over a suitable catalyst (from the group Pd, Pt, Rh, or Ni) to form the corresponding saturated carbonyl compound III. A specific embodiment of this invention is the condensation of propionaldehyde with indancarbaldehyde/indan-2-yl-carbaldehyde, followed by catalytic hydrogenation to form the corresponding indanylmethyl propanal derivatives V.
3. Ether derivatives:
For these derivatives, a mixture of indanmethanol and indan-2-yl-methanol is reacted with an equivalent of a metal hydride (M=sodium, potassium, or lithium) and 1 to 2 equivalents of alkyl or alkenyl halide (R=methyl, ethyl, propyl, allyl, or 2-methylallyl, Y=chloride, bromide, iodide) in the presence of an inert solvent (such as tetrahydrofuran, dioxane, methylene chloride, toluene, and others) at a temperature ranging from 50° C. to 150° C.
Alternatively, the above ethers may be formed by reaction of the indan/indanyl carbaldehyde mixture with 1-2 equivalents of an alkyl or alkenyl halide, and 1-2 equivalents of an aqueous solution (25-50%) of a metal hydroxy base, in the presence of a phase transfer agent (1-10% by weight of the indanmethanol mixture) and an inert solvent (THEF, toluene, methylene chloride, etc.). The temperature may vary between 45° C. and 90° C. Those skilled in the art will understand that a phase transfer agent refers to a tetralkyl ammonium salt where R
1
through R
4
may be the same or different saturated alkyl group, selected from C
1
and through C
8
, and Y represents chloride, bromide, iodide, or sulfate.
In a specific embodiment of this invention, the indanmethanol mixture is reacted with allyl halide or a methallyl halide to form the corresponding ethers, VI and VII, respectively:
The odor characteristics of the specific chemicals presented in this invention are summarized in the following table.
Odor Description
—CHO
green, floral, zesty

caryophyllene, carrot, celery, woody, sassafras

—CH
2
OH
green tea, rosy, musky, wood

floral, rosy with precious wood undertones

green, woody, ozone

green, woody, terpenic

green, spicy, floral cinnamic

green, hyacinth, galbanum, rhubarb

woody, fruity, green, leafy, fresh

floral, rose, woody
The use of the these compounds is widely applicable in current perfumery products, including the preparation of perfumes and colognes, the perfuming of personal care products such as soaps, shower gels, and hair care products as well as air fresheners and cosmetic preparations. The present invention can also be used to perfume cleaning agents, such as, but not limited to detergents, dishwashing materials, scrubbing compositions, window cleaners and the like.
In these preparations, the compounds of the present invention can be used alone or in combination with other perfuming compositions, solvents, adjuvants and the like. The nature and variety of the other ingredients are known by those with skill in the art.
Many types of fragrances can be employed in the present invention, the only limitation being the compatibility with the other components being employed. Suitable fragrances include but are not limited to fruits such as almond, apple, cherry, grape, pear, pineapple, orange, strawberry, raspberry; musk, flower scents such as lavender-like, rose-like, iris-like, carnation-like. Othe

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