IP Library › Granted Patent US 12,723,012
Granted Patent B2
US 12,723,012 · App. 18/269,127 · Granted Sep 1, 2026

Process of making organic compounds

Inventors: Fridtjof Schröder (Hettlingen, CH); Eric Eichhorn (Zürich, CH)
Assignee: GIVAUDAN SA
C07C29/147B01J31/20B01J31/2409C07C29/09C07C51/08C07C51/09C07C231/065C07C233/09B01J2231/40B01J2531/821
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Quick Facts
Patent No.
US 12,723,012
App. No.
18/269,127
Granted
Sep 1, 2026
Kind
B2
Abstract

There is provided a method for preparing homofarnesol (1), the method comprising the steps of: a) providing homofarnesylnitrile (2); b) reacting homofarnesylnitrile (2) to homofarnesic acid (3); and c) reacting homofarnesic acid (3) to homofarnesol (1), wherein the configuration of the double bonds in the compounds 1, 2 and 3 is preserved.

Claims (35)

1 . A method for preparing homofarnesol (1)

the method comprising the steps of:

a) providing homofarnesylnitrile (2)

b) reacting homofarnesylnitrile (2) to homofarnesic acid (3)

 and

c) reacting homofarnesic acid (3) to homofarnesol (1),

wherein the configuration of the double bonds in the compounds 1, 2 and 3 is preserved,

wherein step b is selected from:

i) an enzymatic hydrolysis by a nitrilase or

ii) proceeds in two steps via homofarnesylamide (4)

2 . The method according to claim 1 , wherein the EZ ratio of the double bond at C3 of homofarnesol (1) is greater than 80:20.

3 . The method according to claim 1 , wherein the homofarnesylamide (4) is obtained by hydrolysis of the homofarnesylnitrile (2) with K 2 CO 3 in DMSO and oxidation with H 2 O 2 .

4 . The method according to claim 1 , wherein the homofarnesylamide (4) is obtained by oxidation using metal catalysts.

5 . The method according to claim 1 , wherein step b) is carried out as a one-pot reaction.

6 . The method according to claim 1 , wherein step c) proceeds in two steps via homofarnesic ester (5)

wherein R is a C1 to C20 alkyl group.

7 . The method according to claim 2 , wherein the EZ ratio of the double bond at C3 of homofarnesol (1) is greater than 85:15.

8 . The method according to claim 2 , wherein the EZ ratio of the double bond at C3 of homofarnesol (1) is greater than 90:10.

9 . The method according to claim 6 , wherein R is Methyl or Ethyl.

10 . A method for preparing homofarnesol (1)

the method comprising the steps of:

a) providing homofarnesylnitrile (2)

b) reacting homofarnesylnitrile (2) to homofarnesic acid (3)

 and

c) reacting homofarnesic acid (3) to homofarnesol (1),

wherein the configuration of the double bonds in the compounds 1, 2 and 3 is preserved,

wherein step b) proceeds in two steps via homofarnesylamide (4)

11 . A method for preparing homofarnesol (1)

the method comprising the steps of:

a) providing homofarnesylnitrile (2)

b) reacting homofarnesylnitrile (2) to homofarnesic acid (3)

 and

c) reacting homofarnesic acid (3) to homofarnesol (1),

wherein the configuration of the double bonds in the compounds 1, 2 and 3 is preserved,

wherein step b) is an enzymatic hydrolysis by a nitrilase.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 22, 2023
From: SCHRÖDER, FRIDTJOF; EICHHORN, ERIC
To: GIVAUDAN SA
Reel/Frame 064030/0734 →
Priority Claims (1)
GB 2020331 · Dec 22, 2020 · national
Continuity (1)
Related Publication 20240059636A1 · Feb 22, 2024
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