Alicyclic esters having a musky smell
View Patent ↗The invention relates to novel alicyclic esters, methods for the their preparation, their use as fragrances and also perfumed products and fragrance mixtures containing the compounds according to the invention.
1. A compound of the formula (I)
where
a) R 1 =CH 3 , R 3 =H or CH 3 and R 2 and R 4 =H,
R 5 and R 6 —independently of one another—are H or CH 3 and
Y=—CR 7 R 8 OCOR 9 , where R 7 and R 8 —independently of one another—are H or CH 3 and
R 9 is a branched or straight-chain C 1 to C 5 alkyl group or a branched or straight-chain C 2 to C 5 alkylene group, or
b) R 1 and R 2 —independently of one another—are CH 3 or CH 2 CH 3 ,
R 3 and R 4 —independently of one another—are H or CH 3 ,
R 5 and R 6 together are oxygen and
Y=—CR 7 R 8 OCOR 9 , where R 7 , R 8 and R 9 have the abovementioned meaning, or
R 1 and R 2 —independently of one another—are CH 3 or CH 2 CH 3 ,
R 3 is H or CH 3 ,
R 4 is CH 3 ,
R 5 and R 6 together are oxygen, and
Y=R 9 , where R 9 has the above meaning, or
c) R 1 and R 2 —independently of one another—are CH 3 or CH 2 CH 3 ,
R 3 , R 4 , R 5 and R 6 —independently of one another—are H or CH 3 and
Y=—CR 7 R 8 OCOR 9 , where R 7 , R 8 and R 9 have the abovementioned meaning.
2. The compound according to claim 1 of the formula (IV)
where
R 3 and R 4 —independently of one another—are H or CH 3 ,
R 5 and R 6 together are oxygen, and
Y=—CR 7 R 8 OCOR 9 , where R 7 , R 8 and R 9 have the meaning given in claim 1 or
R 3 is H or CH 3 ,
R 4 is CH 3 ,
R 5 and R 6 together are oxygen, and
Y=R 9 , where R 9 has the meaning given in claim 1 .
3. The compound according to claim 1 of the formula (VI)
where
R 3 =H or CH 3 ,
R 5 and R 6 —independently of one another—are H or CH 3 , and
Y=—CR 7 R 8 OCOR 9 , where R 7 , R 8 and R 9 have the meaning given in claim 1 .
4. The compound according to claim 1 , wherein said compound is 2-(1-cyclohexylethoxy)-2-methylpropyl propionate, 2-[1-(3,3-dimethylcyclohexyl)-1-methylethoxy]-2-oxoethyl propionate or 2-[1-(3,3-dimethylcyclohexyl)-1-methylethoxy]-2-oxoethyl acetate.
5. A method for the preparation of the compound according to claim 1 by reacting a substituted cyclohexylalkanol of the formula
with
a) carboxylic acids of the formula
where
R 1 and R 2 —independently of one another—are CH 3 or CH 2 CH 3 ,
R 3 and R 4 —independently of one another—are H or CH 3 ,
R 5 and R 6 together are hydrogen and
Y=—CR 7 R 8 OCOR 9 where R 7 , R 8 and R 9 have the meaning given in claim 1 , or
b) carboxylic acids R 9 —COOH or carboxylic anhydrides (R 9 —CO) 2 O where
R 1 and R 2 —independently of one another—are CH 3 or CH 2 CH 3 ,
R 3 and R 4 —independently of one another—are H or CH 3 ,
R 5 and R 6 together are oxygen, and
Y=—CR 7 R 8 OCOR 9 , where R 7 , R 8 and R 9 have the above mentioned meaning, or
R 1 and R 2 —independently of one another—are CH 3 or CH 2 CH 3 ,
R 3 is H or CH 3 ,
R 4 is CH 3 ,
R 5 and R 6 together are oxygen, and
Y=R 9 , where R 9 has the above meaning, or
c) epoxides of the formula
where
R 1 =CH 3 , R 3 =H or CH 3 and R 2 and R 4 =H,
R 5 and R 6 —independently of one another—are H or CH 3 and
Y=—CR 7 R 8 OCOR 9 , where R 7 , R 8 and R 9 have the abovementioned meaning, or
R 1 and R 2 —independently of one another—are CH 3 or CH 2 CH 3 ,
R 3 , R 4 , R 5 and R 6 —independently of one another—are H or CH 3 , and
Y=—CR 7 R 8 OCOR 9 , where R 7 , R 8 and R 9 have the meaning given in claim 1 , or
d) a carboxylic acid XCR 7 R 8 —COOH or a carboxylic anhydride (XCR 7 R 8 —CO) 2 O in a first step and with R 9 —COOZ or (R 9 —CO) 2 O in a second step where
R 1 and R 2 —independently of one another—are CH 3 or CH 2 CH 3 ,
R 3 and R 4 —independently of one another—are H or CH 3 ,
R 5 and R 6 together are oxygen, and
Y=—CR 7 R 8 OCOR 9 , where R 7 , R 8 and R 9 have the meaning given in claim 1 ,
X=halogen or OH,
Z=alkali metal or H.
6. A fragrance mixture comprising one or more compounds according to claim 1 and a carrier.
7. A perfumed product comprising one or more compounds according to claim 1 and a carrier.
8. The compound according to claim 2 wherein R 4 =methyl.
9. The compound according to claim 2 wherein R 9 =methyl, ethyl or n-propyl.
10. The compound according to claim 3 wherein R 5 and R 6 =methyl.
11. The compound according to claim 3 wherein R 9 =methyl, ethyl or n-propyl.