Photolabile pro-fragrances

Patent metadata

Field	Value
Publication number	US-9593063-B2
Application number	US-201514949162-A
Country	US
Kind code	B2
Filing date	Nov 23, 2015
Priority date	May 29, 2013
Publication date	Mar 14, 2017
Grant date	Mar 14, 2017

Abstract

The present invention relates to a method for producing photocleavable scent precursors, to products containing the scent precursors, and to the use of the scent precursors for prolonging the scent impression in the product and on surfaces treated with the product.

First claim

What is claimed is:

1. A method for producing a ketone of general formula (I),

where R1, R2, R3, R4 and R5, independently of one another, can each denote hydrogen, —NO 2 , a linear or branched, substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, a linear or branched, substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a cycloalkyl, acyl, aryl or heteroaryl group having 1 to 15 carbon atoms, —OH, —NH 2 , halogen, —NH-alkyl, —N(alkyl) 2 or —N + (alkyl) 3 , or R1 and R2, or R2 and R3, can denote a bridging substituted or unsubstituted cycloalkyl, cycloalkenyl, aryl or heterocycle residue, and
R6 and R7, independently of one another, denote a secondary, tertiary or quaternary C-atom, and
Q denotes an R6 and R7 bridging substituted or unsubstituted group having 1 to 10 carbon atoms,
characterized in that
a) a ketone of general formula (II)

where the groups R6, R7 and Q are identical to general formula (I),
in the presence of a phosphonate of general formula (III),

where R8 and R9, independently of one another, each denote a linear or branched, substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, is reacted with a benzonitrile of general formula (IV),

where the groups R1, R2, R3, R4 and R5 are identical to general formula (I), and subsequently
b) the alpha,beta-unsaturated ketone of general formula (V) obtained in step a),

where the groups R1 to R7 and Q are identical to general formula (I), is selectively hydrogenated to yield a ketone of general formula (I).

2. The method according to claim 1 , characterized in that the ketone of general formula (II) comprises at least one semicyclic or exocyclic double bond.

3. The method according to claim 1 , characterized in that the bridging portion —CH—R7-QR-6- of the ketone of general formula (II) is a hydrocarbon.

4. The method according to claim 1 , characterized in that the ketone of general formula (II) is dihydrocarvone.

5. The method according to claim 1 , characterized in that the groups R8 and R9 of the phosphonate of general formula (III), independently of one another, are each methoxy, ethoxy, propoxy, butoxy or isopropoxy residues.

6. The method according to claim 1 , characterized in that the groups R1 to R5, independently of one another, each denote hydrogen, methyl groups or methoxy groups.

7. The method according to claim 1 , characterized in that the hydrogenating agent is selected from the group of alkali metal borohydrides.

8. A ketone of general formula (VI)

where R1, R2, R3, R4 and R5, independently of one another, can each denote hydrogen, —NO 2 , a linear or branched, substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, a linear or branched, substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a cycloalkyl, acyl, aryl or heteroaryl group having 1 to 15 carbon atoms, —OH, —NH 2 , halogen, —NH-alkyl, —N(alkyl) 2 or —N + (alkyl) 3 , or R1 and R2, or R2 and R3, can denote a bridging substituted or unsubstituted cycloalkyl, cycloalkenyl, aryl or heterocycle residue, producible by
a) reacting dihydrocarvone with a benzonitrile of general formula (IV)

where the groups R1, R2, R3, R4 and R5 are identical to general formula (VI), in the presence of a phosphonate of general formula (III),

where R8 and R9, independently of one another, each denote a linear or branched, substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, and subsequently
b) selectively hydrogenating the alpha,beta-unsaturated ketone obtained in step a) to yield a ketone of general formula (VI).

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Gerke Thomas
• Kropf Christian
• Huchel Ursula
• Griesbeck Axel
• Porschen Bjoern

Classifications

• C07C45/44

  by reduction and hydrolysis of nitriles · CPC title

• C07C49/798 Primary

  containing rings other than six-membered aromatic rings · CPC title

• C07C2101/14

  Chemistry & Metallurgy · mapped topic

• C07C45/45

  by condensation · CPC title

• C07C45/62

  by hydrogenation of carbon-to-carbon double or triple bonds · CPC title