Process for producing muscone and its intermediate
AssigneeTakasago International Corporation
InventorsYoo Tanabe, Tomonori Misaki, Ryohei Nagase, Kunshi Matsumoto
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Abstract
The present invention provides a process for producing a muscone represented by (1) by subjecting a citronellic acid derivative and an undecenoate to a Claisen condensation reaction to produce a keto ester compound represented by (2) decarboxylating the keto ester compound to produce 2,6-dimethyl-8-oxy-2,17-heptadecadiene, cyclizing the heptadecadiene using a metathesis catalyst to produce a 6-dehydromuscone represented by (3) and then hydrogenating the double bond. The present invention also provides the keto ester compound.
Claims14
A process for producing a muscone represented by the following formula (6):
- the process comprising:
- (a) subjecting a citronellic acid derivative represented by the general formula (1):
- wherein X represents a hydroxyl group or a halogen atom, and an undecenoate represented by the following general formula (2):
- wherein R represents a lower alkyl group, to a Claisen condensation reaction, to produce a keto ester compound represented by the following general formula (3):
- wherein R has the same meaning as above,
- (b) decarboxylating the keto ester compound of formula (3) to produce 2,6-dimethyl-8-oxy-2,17-heptadecadiene represented by the following formula (4):
- (c) cyclizing the heptadecadiene of formula (4) using a metathesis catalyst to produce a 6-dehydromuscone represented by the following formula (5)
- wherein the wavy line shows that a sixth-position double-bond cis-isomer and/or trans-isomer is contained, and
- (d) hydrogenating the double bond of the 6-dehydromuscone of formula (5).
A process for producing a (R)-muscone represented by the following formula (6-a):
- the process comprising:
- (a) subjecting a (R)-citronellic acid derivative represented by the general formula (I-a):
- wherein X represents a hydroxyl group or a halogen atom, and an undecenoate represented by the following general formula (2):
- wherein R represents a lower alkyl group, to a Claisen condensation reaction, to produce a (6R)-keto ester compound represented by the following general formula (3-a):
- wherein R has the same meaning as above,
- (b) decarboxylating the keto ester compound of formula (3-a) to produce (6R)-2,6-dimethyl-8-oxy-2,17-heptadecadiene represented by the following formula (4-a):
- (c) cyclizing the heptadecadiene of formula (4-a) using a metathesis catalyst to produce a (R)-6-dehydromuscone represented by the following formula (5-a)
- wherein the wavy line shows that a sixth-position double-bond cis-isomer and/or trans-isomer is contained, and
- (d) hydrogenating the double bond of the (R)-6-dehydromuscone of formula (5-a).
A process for producing a keto ester compound represented by the following general formula (3):
- wherein R represents a lower alkyl group, the process comprising subjecting a citronellic acid derivative represented by the general formula (1):
- wherein X represents a hydroxyl group or a halogen atom, and an undecenoate represented by the following general formula (2):
- wherein R has the same meaning as above, to a Claisen condensation reaction.
A process for producing a (6R)-keto ester compound represented by the following general formula (3-a):
- wherein R represents a lower alkyl group, the process comprising subjecting a (R)-citronellic acid derivative represented by the following general formula (I-a):
- wherein X represents a hydroxyl group or a halogen atom, and an undecenoate represented by the following general formula (2):
- wherein R has the same meaning as above, to a Claisen condensation reaction.
A keto ester compound represented by the following general formula (3):
- wherein R represents a lower alkyl group.
A (6R)-keto ester compound represented by the following general formula (3-a):
- wherein R represents a lower alkyl group.
Dependencies are inferred from the claim text.