Process of making organic compounds
There is provided a method for preparing homofarnesol (1), the method comprising the steps of: a) providing farnesyl chloride (2) b) reacting farnesyl chloride (2) to homofarnesate (3) by alkoxycarbonylation; and c) reacting homofarnesate (3) to homofarnesol (1), wherein the configuration of the double bonds in the compounds 1, 2 and 3 is preserved.
1 . A method for preparing homofarnesol (1)
the method comprising the steps of:
a) providing farnesyl chloride (2)
b) reacting farnesyl chloride (2) to homofarnesate (3) by alkoxycarbonylation in the presence of palladium on carbon as catalyst in aqueous alcohol under CO atmosphere
and
c) reacting homofarnesate (3) to homofarnesol (1),
wherein R is a C 1 -C 10 alkyl group; and
wherein the configuration of the double bonds in the compounds 1, 2 and 3 is preserved.
2 . The method according to claim 1 , wherein farnesyl chloride (2) is provided in a mixture with carbamate (6),
wherein R′ is an alkyl group selected from Me, Et, n-Pr, and the two R″ residues are same or different alkyl groups selected from Me, Et, n-propyl, i-propyl, n-butyl, i-butyl, or the two R″ residues form together a ring system.
3 . The method according to claim 2 , wherein the two R″ residues of carbamate (6) are the same alkyl groups selected from Et and n-propyl.
4 . The method according to claim 1 , wherein the E/Z ratio of the double bond at C3 of homofarnesol (1) is greater than 80:20.
5 . The method according to claim 1 , wherein R is Me or Et.
6 . The method according to claim 1 , wherein the reaction of homofarnesate (3) to homofarnesol (1) is a reduction.
7 . The method according to claim 1 , wherein the alkoxycarbonylation is carried out in the presence of a phase transfer catalyst.
8 . The method according to claim 1 , wherein R is selected from at least one of Me, Et, n-propyl, i-propyl, n-butyl, or i-butyl.
9 . The method according to claim 1 , wherein R includes one or more ring systems.
10 . The method according to claim 1 , wherein R is substituted.
11 . The method according to claim 2 , wherein R′ is substituted.
12 . The method according to claim 2 , wherein the ring system comprises morpholine, pyrrolidine or combinations thereof.
13 . The method according to claim 2 , wherein the two R″ residues are substituted.
14 . The method according to claim 4 , wherein the E/Z ratio of the double bond at C3 of homofarnesol (1) is greater than 85:15.
15 . The method according to claim 4 , wherein the E/Z ratio of the double bond at C3 of homofarnesol (1) is greater than 90:10.