New access to pseudo-ionones and pseudo-iso-methyl ionones from geranyl derivatives

Article abstract of DOI:10.1081/SCC-120016368

Pseudo-ionones and pseudo-iso-methyl ionones, precursors of fragrant derivatives were obtained from geranyl chloride, an industrially available starting material.

Full text of DOI:10.1081/SCC-120016368

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New Access to Pseudo-ionones andPseudo- iso -methyl
Ionones from Geranyl Derivatives
B. Boulin a , B. Arreguy-San Miguel b & B. Delmond a
a Laboratoire de Chimie des Substances Végétales , Institut du Pin , Université Bordeaux 1 ,
Talence Cedex, France
b Unité d'Enseignement et de Recherche des Sciences Pharmaceutiques , Université Bordeaux
2 , France
Published online: 17 Aug 2006.
To cite this article: B. Boulin , B. Arreguy-San Miguel & B. Delmond (2003) New Access to Pseudo-ionones andPseudo- iso -
methyl Ionones from Geranyl Derivatives, Synthetic Communications: An International Journal for Rapid Communication of
Synthetic Organic Chemistry, 33:6, 1047-1055, DOI: 10.1081/SCC-120016368
To link to this article: http://dx.doi.org/10.1081/SCC-120016368
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SYNTHETIC COMMUNICATIONSÕ
Vol. 33, No. 6, pp. 1047–1055, 2003
New Access to Pseudo-ionones and
Pseudo-iso-methyl Ionones from
Geranyl Derivatives
B. Boulin,1 B. Arreguy-San Miguel,2 and B. Delmond1,
*
1Laboratoire de Chimie des Substances Vegetales,
Institut du Pin, Universite Bordeaux 1,
Talence Cedex, France
2Unite d’Enseignement et de Recherche des Sciences
Pharmaceutiques, Universite Bordeaux 2, France
ABSTRACT
Pseudo-ionones and pseudo-iso-methyl ionones, precursors of
fragrant derivatives were obtained from geranyl chloride,
an industrially available starting material.
Key Words: Ionones; Pseudo-ionones; Pseudo-iso-methyl ionones;
Geranyl derivatives; Terpenes; Aroma; Sulfoxides.
*Correspondence: B. Delmond, Laboratoire de Chimie des Substances
Vegetales, Institut du Pin, Universite Bordeaux 1, 351 cours de la Liberation
33405 Talence Cedex, France; E-mail: b.delmond@lcsv.u-bordeaux1.fr.
1047
DOI: 10.1081/SCC-120016368
Copyright & 2003 by Marcel Dekker, Inc.
0039-7911 (Print); 1532-2432 (Online)
www.dekker.com

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1048
Boulin, Arreguy-San Miguel, and Delmond
INTRODUCTION
Pseudo-ionone (6,10-dimethyl-3,5,9-undecatrien-2-one) 1, is an
unsaturated ketone, and very useful as a key intermediate in natural
product synthesis. In particular, its cyclisation to ionones has received
much attention because of the industrial importance of b-ionone forthe
synthesis of retinoids (vitamin A),[1] carotenoids (b-carotene)[2] and
odorant compounds.[3]
Various methods have been reported for the synthesis of pseudo-
ionone, but the most industrially used are based on the reactivity of
citral (aldolisation),[4] dehydrolinalol (Carroll[5] and Saucy-Marbet
reactions[6]) and myrcene.[7]
RESULTS
In previous communications,[8] we have used thioderivatives towards
the synthesis of fragrant terpenic compounds and retinoids. In particular,
sulfoxides which are widely used in synthetic chemistry,[9] because of the
ability of sulfurto stabilize a-carbanions allowing C-C coupling reac-
tions. On the other hand, the sulfinyl moiety can be removed by pyrolysis,
which represents a very useful method of generating a double bond. In
connection with this work, we would like to propose an easy synthesis of
pseudo-ionone 1 and pseudo-iso-methyl ionone 2 (Fig. 1) from
commercial geranyl chloride (E/Z 60:40) 3.
We describe in this report a synthetic scheme established from each
isomers (geranyl chloride 3a and neryl chloride 3b).
When the geranyl chloride 3a was treated with the a-anion of phenyl
sulfinyl acetone (generated from the reaction of the latter with sodium
Figure 1.

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Pseudo-ionones and Pseudo-iso-methyl Ionones
1049
Scheme 1.
hydride in THF at 0ꢀC), the C13-keto sulfoxide 4a (Sch. 1; x ¼ 1) was
formed. However, sulfoxide 4a could not be isolated at room tempera-
ture, because of the elimination of phenyl sulfenic acid. The crude
sulfoxide 4a was immediately refluxed in carbon tetrachloride in the pres-
ence of sodium carbonate to give pseudo-ionone 1a in 36% overall yield.
a-Phenyl sulfenyl acetone reagent (Sch. 1; x ¼ 0), has been used as
homologation synthon. Under these conditions, treatment of geranyl
chloride 3a with the a-sulfenyl carbanion derivated (NaH/THF reflux)
from phenyl sulfenyl acetone, gave the corresponding C13-keto sulfide 4a
(x ¼ 0) (Rdt 68%).
To overcome the problems of the low reactivity of geranyl chloride,
but also of the low stability of keto sulfoxide derivatives, the geranyl
iodide has been used, in situ generated by a preliminary treatment of
geranyl chloride with sodium iodide.
Thus alkylation of the anion of phenyl sulfenyl acetone with geranyl
chloride 3a in the presence of sodium iodide took place smoothly at low
temperature (0ꢀC) to give with good yields C13-keto sulfide 5a, which can
be easily isolated and purified (Sch. 2).
Subsequent m-chloroperbenzoic acid (MCPBA) oxidation of the
sulfide group to the sulfoxide and pyrolysis of the a-sulfinyl carbonyl
intermediate as early described (CCl4 reflux/NaHCO3) gave pseudo-
ionone 1a (6,10-dimethyl-3E,5E,9-undecatrien-2-one) in an overall yield
of 84% from geranyl chloride 3a.
From neryl chloride 3b, similarresults were obtained using the same
sequence; thus via corresponding C13-keto sulfide intermediate 5b,
the pseudo-ionone 1b (6,10-dimethyl-3E,5Z,9-undecatrien-2-one) was
prepared in 82% overall yield.
The double-bond configurations of pseudo-ionones 1a and 1b were
1
based on the observation of the H NMR signals of the respective H-3

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Boulin, Arreguy-San Miguel, and Delmond
Scheme 2.
Scheme 3.
protons at ꢀ ¼ 5.94 ppm and 6.00 ppm respectively. An (E)-configuration
was assigned to 3,4-double bond from measurements of the coupling
constants (J3,4 ¼ 15.3 Hz). This trans-configuration for the newly
formed double-bond is in accordance with a sulfenic acid syn-elimination
mechanism.[9]
The observed values at ꢀ ¼ 17.3 ppm and ꢀ ¼ 24.6 ppm forC-13
methyl carbon resonances in the 13C NMR spectra for 1a and 1b were
indicative of the (5E) and (5Z) double bond configuration respectively.
Using an analogous approach, we undertook the preparation of
pseudo-iso-methyl ionone 2, the precursor of iso-methyl ionone. Iso-
methyl ionone is the isomer most wanted by perfumers because of its
fine violet fragrance.
Also, we reported an efficient and specific access to pseudo-iso-
methyl ionones from geranyl and neryl chlorides (Sch. 3).
Anion generation (NaH/THF) from C13-keto sulfides 5a and 5b
previously obtained from respectively geranyl and neryl chlorides,
elongation by coupling with methyl iodide, afforded almost quantita-
tively, the corresponding C14-keto sulfides 6a and 6b.

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Pseudo-ionones and Pseudo-iso-methyl Ionones
1051
Afteroxidation (MCPBA) of sulfide group to sulfoxide then sulfox-
ide thermolysis (CCl4 reflux/NaHCO3) the pseudo-iso-methyl ionones
2a and 2b were obtained with an overall yield of 82% and 80%
respectively from geranyl chloride 3a and neryl chloride 3b.
CONCLUSION
On the basis of these results, commercially available geranyl chloride
is key intermediate for the synthesis of pseudo-ionones and pseudo-iso-
methyl ionone.
EXPERIMENTAL SECTION
Purification of the products were achieved by flash-chromatography
1
(neutral alumina Merck). H NMR and 13C NMR spectra were recorded
on a Bruker AC 250 spectrometer. High-resolution mass spectra (HRMS)
data were recorded at an ionizing voltage of 70 eV on a Micromass
AutoSpec.
Synthesis of Pseudo-ionones 1a and 1b
To a suspension of 95% sodium hydride (6.4 mmol) in THF (6 mL),
was added at 0ꢀC and under nitrogen atmosphere, phenyl sulfenyl
acetone (1.058 g, 6.4 mmol) in THF (6 mL). The solution was stirred
for 30 min, geranyl chloride 3a (1 g, 5.8 mmol) and sodium iodide
(1.738 g, 11.6 mmol) in THF solution (6 mL) were added. The mixture
was stirred for 12 h, hydrolysed with aqueous saturated NH4Cl solution
and extracted with CHCl3. The combined organic layers were washed
with aqueous saturated NaCl, dried over MgSO4 and evaporated under
reduced pressure. Further purification was performed by alumina column
chromatography. Elution with petroleum ether/ether (9:1) gave 1.54 g
(88% yield) of C13-keto sulfide (6,10-dimethyl-3-phenylthio-5E,9-undeca-
dien-2-one) 5a.
ꢀ
H (CDCl3) 1.59 (3H, s), 1.60 (3H, s), 1.67 (3H, s), 2.05 (4H, m), 2.47
(2H, m), 2.22 (3H, s), 3.65 (1H, t), 5.07 (1H, t, J ¼ 6.7 Hz), 5.15 (1H, t,
J ¼ 7.0 Hz), 7.20–7.40 (5H, Ph); ꢀC (CDCl3) 16.3 (CH3-13), 17.7 (CH3-
12), 25.7 (CH3-11), 26.5 (CH2-8), 26.9 (CH2-1), 29.1 (CH2-4), 39.7 (CH2-
7), 57.6 (CH-3), 119.8 (CH-5), 124.0 (CH-9), 127.9 (CH, Ph), 129.1

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Boulin, Arreguy-San Miguel, and Delmond
(CH, Ph), 131.5 (C-10), 132.6 (CH, Ph), 133.1 (C-6), 138.5 (C, Ph), 205.0
(C-2); HRMS (C19H26OS): Calcd. 302.1691, found 302.1692.
To a cooled (À78ꢀC) solution of C13-keto sulfide 5a (302 mg, 1 mmol)
in CH2Cl2 (20 mL), m-chloroperoxybenzoic acid (1 mmol) in CH2Cl2
(10 mL) was added. The reaction mixture was stirred for 3 h, hydrolysed
with 5% sodium bisulfite, then extracted with CH2Cl2. The organic layers
were washed with saturated NaHCO3 solution and NaCl solution, dried
(MgSO4) and evaporated under reduced pressure.
The crude product in CCl4 solution (10 mL) was refluxed for 5 h in
the presence of NaHCO3 (84 mg, 1 mmol). The reaction mixture was
poured into water and extracted with ether. The organic layer was
washed, dried and concentrated under reduced pressure to give a crude
product which was purified by alumina column chromatography. Elution
with petroleum ether/ether (8:2) provided pseudo-ionone 1a [(3E,5E)-
6,10-dimethyl-3,5,9-undecatrien-2-one] (182 mg, 95% yield).
ꢀH (CDCl3) 1.47 (3H, s), 1.54 (3H, s), 1.78 (3H, s), 2.03 (4H, m), 2.13
(3H, s), 4.95 (1H, t), 5.87 (1H, d, J ¼ 11.3 Hz), 5.94 (1H, d, J ¼ 15.3 Hz),
7.37 (1H, dd, J ¼ 11.3 Hz, J0 ¼ 15.3 Hz); ꢀC (CDCl3) 17.3 (CH3-13), 17.6
(CH3-12), 25.6 (CH3-11), 26.2 (CH2-8), 27.3 (CH3-1), 40.3 (CH2-7), 123.2
(CH-9), 123.7 (CH-5), 128.4 (CH-3), 132.0 (C-10), 139.4 (CH-4),
150.9 (C-6), 198.4 (C-2); HRMS (C13H20O): Calcd. 192.1514, found
192.1510.
From neryl chloride 3b, according to the same procedure, we
obtained pseudo-ionone 1b [(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-
one] (82% yield).
ꢀH (CDCl3) 1.57 (3H, s), 1.63 (3H, s), 1.86 (3H, s), 2.11 (2H, m), 2.22
(3H, s), 2.24 (2H, m), 5.07 (1H, m), 5.96 (1H, d, J ¼ 11.6 Hz), 6.00 (1H, d,
J ¼ 15.3 Hz), 7.40 (1H, dd, J ¼ 11.6 Hz, J0 ¼ 15.3 Hz); ꢀC (CDCl3) 17.7
(CH3-12), 24.6 (CH3-13), 25.7 (CH3-11), 26.8 (CH2-8), 27.3 (CH3-1),
32.9 (CH2-7), 123.2 (CH-9), 124.6 (CH-5), 128.2 (CH-3), 132.6 (C-10),
139.5 (CH-4), 151.2 (C-6), 198.8 (C-2); HRMS (C13H20O): Calcd.
192.1514, found 192.1510.
Synthesis of Pseudo-iso-methyl Ionones 2a and 2b
To a suspension of sodium hydride (53 mg, 2.2 mmol) in THF
solution (4 mL), was added at 0ꢀC a solution of C13-keto sulfide 5a
(600 mg, 2 mmol) in THF (3 mL). The mixture was stirred for 30 min at
0ꢀC, and then iodomethane (563 mg, 4 mmol) was added. The reaction
mixture was kept under stirring for 12 h, hydrolysed with aqueous
saturated NH4Cl solution and extracted with CHCl3. The combined

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Pseudo-ionones and Pseudo-iso-methyl Ionones
1053
organic layers were washed with aqueous saturated NaCl, dried over
MgSO4 and evaporated under reduced pressure. The purification of
the crude product was performed by alumina column chromatography.
Elution with petroleum ether/ether (9:1) gave 600 mg (98% yield) of C14-
keto sulfide 6a.
ꢀ
H (CDCl3) 1.30 (3H, s), 1.59 (3H, s), 1.61 (3H, s), 1.69 (3H, s), 2.05
(4H, m), 2.37 (3H, s), 2.50 (2H, m), 5.05 (2H, m), 7.20–7.40 (5H, Ph); ꢀC
(CDCl3) 16.5 (CH3-13), 17.7 (CH3-12), 20.9 (CH3-14), 24.9 (CH3-1), 25.7
(CH3-11), 26.5 (CH2-8), 35.3 (CH2-4), 39.9 (CH2-7), 60.4 (C-3), 118.6
(CH-5), 124.1 (CH-9), 128.9 (CH, Ph), 129.3 (CH, Ph), 130.9 (C-6),
131.5 (C-10), 136.1 (CH, Ph), 138.9 (C, Ph), 205.7 (C-2); HRMS
(C20H28OS): Calcd. 316.1861, found 316.1860.
To a cooled (À78ꢀC) solution of C14-keto sulfide 6a (316 mg, 1 mmol)
in CH2Cl2 (20 mL), m-chloroperoxybenzoic acid (1 mmol) in CH2Cl2
(10 mL) was added. After being stirred for 3 h, the mixture was hydro-
lysed with 5% sodium bisulfite, then extracted with CH2Cl2. The organic
layers were washed with saturated NaHCO3 solution and NaCl solution,
dried (MgSO4) and evaporated under reduced pressure. The crude
product in CCl4 solution (10 mL) was refluxed for 5 h in the presence
of NaHCO3 (84 mg, 1 mmol). The reaction mixture was hydrolysed
with water and extracted with ether. The organic layer was washed
and dried. After concentration under reduced pressure the crude product
was subjected to a purification by alumina column chromatography.
Elution with petroleum ether/ether (8:2) provided pseudo-iso-methyl
ionone 2a [(3E,5E)-3,6,10-trimethyl-3,5,9-undecatrien-2-one] (196 mg,
95% yield).
ꢀ
H (CDCl3) 1.57 (3H, s), 1.65 (3H, s), 1.83 (3H, s), 1.88 (3H, s), 2.16
(4H, m), 2.32 (3H, s), 5.06 (1H, m), 6.17 (1H, d, J ¼ 11.6 Hz), 7.28 (1H, d,
J ¼ 11.6 Hz); ꢀC (CDCl3) 11.1 (CH3-14), 17.4 (CH3-13), 17.6 (CH3-12),
25.5 (CH3-11), 26.5 (CH2-8), 25.5 (CH3-1), 40.8 (CH2-7), 121.3 (CH-5),
123.3 (CH-9), 132.2 (C-10), 134.0 (C-3), 135.2 (CH-4), 148.8 (C-6), 199.9
(C-2); HRMS (C14H22O): Calcd. 206.1670, found 206.1669.
From neryl chloride 3b according to the same procedure, we have
obtained pseudo-iso-methyl ionone 2b [(3E,5Z)-3,6,10-trimethyl-3,5,9-
undecatrien-2-one] (80% overall yield).
ꢀ
H (CDCl3) 1.58 (3H, s), 1.65 (3H, s), 1.83 (3H, s), 1.90 (3H, s), 2.13
(2H, m), 2.27 (2H, m), 2.31 (3H, s), 5.09 (1H, m), 6.18 (1H, d,
J ¼ 11.7 Hz), 7.27 (1H, d, J ¼ 11.7 Hz); ꢀC (CDCl3) 11.2 (CH3-14), 17.7
(CH3-12), 24.9 (CH3-13), 25.4 (CH3-1), 25.5 (CH3-11), 26.9 (CH2-8), 33.0
(CH2-7), 122.1 (CH-5), 123.3 (CH-9), 132.5 (C-10), 133.9 (C-3), 135.2
(CH-4), 148.8 (C-6), 199.7 (C-2); HRMS (C14H22O): Calcd. 206.1670,
found 206.1669.

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Boulin, Arreguy-San Miguel, and Delmond
ACKNOWLEDGMENTS
Sincere thanks are expressed to DRT for a student grant to B. Boulin.
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Received in the UK February 11, 2002

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