Oxidation of the cyclopentanone and cyclohexanone alkyl derivatives in a pseudohomogeneous system without a phase transfer agent

Article abstract of DOI:10.1134/S1070363211080147

The reaction of catalytic oxidation of C₅-C₁₂ alkyl- and cycloalkylcyclopentanones and -cyclohexanones to lactones in a pseudohomogeneous system without the participation of phase transfer agents was investigated. It was established that the catalytic systems prepared on the basis of molybdenum and tungsten blue (MeO_nBr_m, where Me = Mo, W, n = 1, 2, m = 2, 3) and H₃PO₄ deposited on powdered activated carbon AG-3 at 40-60°C, at 5-6 h duration exhibit a high selectivity in the reaction of nucleophilic addition of oxygen to the ketones with the formation of the valero- and caprolactones. Pleiades Publishing, Ltd., 2011.

Full text of DOI:10.1134/S1070363211080147

ISSN 1070-3632, Russian Journal of General Chemistry, 2011, Vol. 81, No. 8, pp. 1664–1670. © Pleiades Publishing, Ltd., 2011.
Original Russian Text © Kh.M. Alimardanov, N.I. Garibov, M.F. Abbasov, O.A. Sadygov, M.Ya. Abdullaeva, N.A. Dzhafarova, 2011, published in Zhurnal
Obshchei Khimii, 2011, Vol. 81, No. 8, pp. 1319–1325.
Oxidation of the Cyclopentanone and Cyclohexanone Alkyl
Derivatives in a Pseudohomogeneous System
without a Phase Transfer Agent
Kh. M. Alimardanov, N. I. Garibov, M. F. Abbasov,
O. A. Sadygov, M. Ya. Abdullaeva, and N. A. Dzhafarova
Mamedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan,
ul. Khodzhaly 30, Baku, 1025 Azerbaijan
e-mail: omar.sadiqov@gmail.com
Received July 20, 2010
Abstract—The reaction of catalytic oxidation of C5–C12 alkyl- and cycloalkylcyclopentanones and -cyclo-
hexanones to lactones in a pseudohomogeneous system without the participation of phase transfer agents was
investigated. It was established that the catalytic systems prepared on the basis of molybdenum and tungsten
blue (MeOnBrm, where Me = Mo, W, n = 1, 2, m = 2, 3) and H3PO4 deposited on powdered activated carbon
AG-3 at 40–60°C, at 5–6 h duration exhibit a high selectivity in the reaction of nucleophilic addition of oxygen
to the ketones with the formation of the valero- and caprolactones.
DOI: 10.1134/S1070363211080147
Higher lactones of C5–C12 composition with alkyl
and cycloalkyl substituents are characterized by
biological activity and are of interest as drugs,
fragrances, and flavoring agents in various cosmetics,
detergents, and cleaning products, soaps and shampoo
[1–6].
In [14] caprolactone was obtained by the intra-
molecular conversion of a mixture of adipic and 6-
hydroxycapronic acid with the participation of oxides
or hydroxides of alkali and alkaline earth metals.
Currently, an extensive study is carried out on the
liquid phase oxidation of C6–C12 cyclic ketones with
various peroxyacids by the Bayer–Villiger reaction
[15]. However, the iperformance of this process on an
industrial scale is associated with some technological
problems caused by the necessity of synthesis and
isolation of peroxyacids, the use of a large amount of
organic and mineral acids, and implementation of
special safety techniques and solving some environ-
mental problems.
In some foods, particularly in butter, coconut oil,
milk, and cream the presence of 6-alkylvalerolactone
was found [7], providing their fragrance. Their
synthetic analogs, N-alkyloctanolactones, have fresh
fruit and strawberry aroma with hints of green
vegetables or whole milk [8].
The above lactones are obtained, in general, by
hydrogenation of dicarboxylic acids and related anhyd-
rides, cyclization of unsaturated hydroxy- and halogen-
substituted carboxylic acids, by reductive cyclization
of aliphatic diols, carboxylation of unsaturated hydro-
carbons, or by the oxidation of various oxygen-contain-
ing compounds [9–12]. In particular, in [13] were syn-
thesized the bicyclic lactones and their derivatives by
[3+2]-cycloaddition of epoxides to the hydrocarbons
with a terminal alkyne group in the presence of a
tungsten complex. For the catalytic oxidation of diols
to lactones vanadium catalysts V2O5, VCl5, and
VO(acac)3 were developed and used in CCl4 [10].
More acceptable results were obtained at the ap-
plication of organic hydroperoxides, hydrogen per-
oxide [16–18], or molecular oxygen [19, 20] in the
presence of different enzymes or complex systems
containing polyvalent metals.
Analysis of published data shows that from the
practical and environmental points of view much
interest provides a way of obtaining the higher C10–C12
lactones by catalytic oxidation of the alicyclic ketones
using hydrogen peroxide and heterogenic catalyst. The
purpose of this study was to examine the oxidation of
1664

OXIDATION OF THE CYCLOPENTANONE AND CYCLOHEXANONE ALKYL DERIVATIVES
1665
alkyl- and cycloalkyl-substituted cyclohexanones and
cyclopentanones by aqueous solution of hydrogen
peroxide or its adducts with urea in pseudohomo-
geneous system with a phosphomolybdenum or phos-
potungsten system highly dispersed on activated carbon,
without the use of phase transfer agents.
Villiger, at the use of ethanol solutions of molybde-
num(V) halides the accumulation of lactones in the
liquid phase takes place with participation of nucleo-
philic oxygen of the more polarized peroxymol-
ibdenium fragment of the catalytic complex through an
intermediate stage of formation of oxirane structure
with the enol form of the substrate followed by its
opening [21].
We have shown previously that in contrast to the
reactions of peroxide oxidation of ketones by Bayer–
O
O
OH
O
OOCR
R1
R1
O
R_C
(1)
RCOOH
+
+
( )n
( )n
( )n
OOH
R1
By preliminary experiments carried out for the estima-
tion of effectiveness of the phosphomolybdenum and
phospotungsten catalysts we synthesized highly
dispersed on activated carbon substances of the com-
position H3PO4·xMoOnBrm/C and H3PO4·xWOnBrm/C
(where x = 1–12, n = 1 , 2, m = 2, 3). In the reactions
of decomposition of aqueous solution of H2O2 or
acetate solution of adduct of H2O2 with urea it was
show that they are fairly active at a temperature of 20–
50°C. It is known that under these conditions a mixture
of peroxy-complexes of different structure is formed in
situ [22]. Therewith, the hydrolysis of the monomeric
or dimeric forms of molybdenum (Mon+) and tungsten
(Wn+) oxobromides accelerates the formation of such
complexes, which are effective carriers of active
oxygen to the substrate [23].
spectrum the signals are detected with g11 = 2.094, g1 =
1.941, A11(Mo) = 82 Gs, A1(Mo) = 31 Gs. The change
in the intensity of the ESR signals depending on the
concentration of MoO3+ in ethanol shows the
predominance in solution of a dimeric form. In the IR
spectrum, the presence of Mo–O–Mo bonds is
characterized by the absorption bands in the region of
830–850 cm–1. At the interaction of the complex with
H2O2 its blue color is transformed to golden-yellow,
and in the infrared spectrum strong absorption bands
appear at 1090, 1055, 860, 770 cm–1 (–O–O– bonds).
The IR spectra obtained for similar compounds of Wn+
correspond to published data [23].
In the IR spectrum of the catalytic system highly
dispersed on the AG-3 activated carbon, in tablets with
KBr, the intensity of the above bands are reduced and
they are shifted to higher frequencies.
In the IR spectrum of ethanol solution of the
molybdenum blue treated with 85% solution of H3PO4
there are the absorption bands of the ion PO43– (1075,
1060, and 1040 cm–1) and Mo = O bond (990, 940, and
910 cm–1). The electron absorption spectra are charac-
terized by the peaks at 14200 cm–1 (20), 21100 cm–1
(400), 24100 cm–1 (2400) and 26500 cm–1 (2000),
indicating the presence of MoO3+ ions. In the ESR
Oxidation of alkyl- and cycloalkylcyclanes at 40–
70°C proceeds in pseudohomogeneous system sub-
strate–catalyst–adduct of carbamide with H2O2, in
acetic acid, yielding 68.2–84.2% of the corresponding
lactones. According to the experimental data, we
suggest that the reaction proceeds along the following
scheme:
O
O
OH
Me
H3[PO4 MeOnBrm]/C +
R1COOH + H2O2 + CO(NH4)2
H
R
R
O
O
HO
O
( )n
( )n
OCOR1
( )n
IIIa_IIIh, IVa_IVh
R
R
( )n
Ia_Ih, IIа_IIh
M = Mo, W; n = 1 (I), 2 (II); R = n-C5H11 (a), n-C6H13 (b), n-C7H15 (c), cyclo-C5H9 (d), cyclo-C6H11 (e), cyclo-C12H23 (f),
bicyclo-C7H11 (g), cyclo-С12Н23 (h).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 81 No. 8 2011

1666
ALIMARDANOV et al.
Table 1. Oxidation of 2-heptylcyclopentanone with hydrogen peroxide in the presence of highly dispersed H3PO4·MeOnBrm
system (n = 1, 2, m = 2, 3) on activated carbon (molar ratio Men+: H3PO4 = 4: 1)
2-Heptylcyclopentanone: H2O2
molar ratio
Reaction
Experiment duration,
h
Conversion of 2-
Selectivity for the
temperature, ºC
heptylcyclopentanone, % 5-heptylvalerolactone, %
Н3РО4·МоОnВrm/С
1:1
40
40
40
40
40
50
60
70
60
60
60
60
5
63.3
66.4
70.0
71.7
75.0
72.0
74.1
73.5
76.2
85.7
90.2
94.1
49.5
52.6
60.1
60.8
54.2
57.7
72.0
56.6
70.0
80.9
75.0
68.0
1:1.5
1:2
5
5
1:3
5
1:4
5
1:1.5
1:1.5
1:1.5
1:1.5
1:1.5
1:1.5
1:1.5
5
5
5
6
7
8
10
Н3РО4·WОnВrm/С
1:1.5
1:2
40
40
40
60
60
5
5
5
6
8
62.5
64.2
72.8
81.0
86.4
57.4
61.0
65.6
83.4
59.7
1:3
1:2
1:2
As seen from Table 1 and Fig. 1, yields of the target
products of the reaction and the selectivity of ketones
oxidation depend on the molar ratio of individual
components in the catalytic complex and the
experimental conditions. Changes in the composition
and structure of the starting ketones do not signi-
ficantly affect the yield of lactones (Table 2). Some
increase in yield of lactones and in the selectivity is
observed in the series: 2-alkylcyclopentanone < 2-
alkylcyclohexanone < 2-cycloalkylcyclopentanone <
2-cycloalkylcyclohexanone < 2-norbornylcyclohexa-
none. The higher yields of 6-norbornylvalerolactone
and 7-norbornylcaprolactone are likely due to the
strained structure of the norbornyl group.
A significant influence on the transformation of
active oxygen and the selectivity of the lactone forma-
tion has a variation in the ratio of H3PO4 and MeOnBrm
in the catalyst (Fig. 1). The effective oxygen carriers in
this case are the complexes formed at the interaction of
90
80
70
60
50
40
30
n+
1 mol of H3PO4 with 4 mol of Mon+ or W by the
scheme (2):
Н3РО4 + 4МеОnВrm + Н2О2
→ {РО4[МеО(О2Вrх)]4}3– + 4(m – х)НВr.
(2)
Further increase in the proportion of the Mon+ and
Wn+ oxobromides in the catalytic system leads only to
an increase in the rate of unproductive decomposition
of H2O2.
1:2
1:4
1:6
1:8
1:10
Mon+:H3PO4, Wn+:H3PO4
Fig. 1. Conversion of (1, 3) 2-heptylcyclopentanone and
(2, 4) selectivity for lactone vs. molar ratio of Mon+: (1, 2)
H3PO4 and (3, 4) Wn+:H3PO4 in the complex (T = 40°C, τ =
5 h, 2-heptylcyclopentanone: H2O2 = 1:1.5).
Previously similar results were obtained for peroxo-
complexes of PW(Mo)xOyz– composition formed in
aqueous medium from the corresponding hetero-
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OXIDATION OF THE CYCLOPENTANONE AND CYCLOHEXANONE ALKYL DERIVATIVES
1667
Table 2. Oxidation of some alkyl and cycloalkyl derivatives of alicyclic ketones with hydrogen peroxide in the presence of
the H3PO4·MoOnBrm system (n = 1, 2, m = 2, 3) highly dispersed on activated carbon (molar ratio Mon+: H3PO4 = 4:1), T =
60ºС, τ = 6 h, ketone: H2O2 = 1:1.5
High-
boiling
residue,
wt %
High-
boiling
residue,
wt %
Ketone
Selectivity
Ketone
Selectivity
Initial ketone
conversion, for lactone,
Initial ketone
conversion, for lactone,
%
%
%
%
2-Pentylcyclopentanone
88.2
86.5
87.1
90.0
91.7
84.3
83.8
86.0
87.0
87.2
16.2
2-Pentylcyclohexanone
89.4
91.0
88.5
89.0
93.3
90.1
92.5
87.0
88.4
87.0
12.2
2-Hexylcyclopentanone
19.4
17.4
16.1
13.4
2-Hexylcyclohexanone
7.8
2-Cyclopentylcyclopentanone
2-Cyclohexylcyclopentanone
2-Cyclopentylcyclohexanone
2-Cyclohexylcyclohexanone
13.9
12.4
14.9
2-Bicyclo[2.2.1]heptylcyclo-
pentanone (2-norbornylcyclo-
pentanone)
2-Bicyclo[2.2.1]heptylcyclo-
hexanone (2-norbornylcyclo-
hexanone)
2-(5-Methylbicyclo[2.2.1]-
heptylcyclopentanone)
86.0
79.4
82.3
85.9
23.6
15.8
2-(5-methylbicyclo[2.2.1]-
heptylcyclohexanone)
2-Dodecylcyclohexanone
87.4
82.1
84.2
85.9
16.0
14.8
2-Dodecylcyclopentanone
polyacid and hydrogen peroxide in combination with
phase transfer catalysts in the reaction of epoxidation
of cycloolefins [23, 24].
the liquid phase takes place in pseudohomogeneous
system that provides high conversion of ketones and
good yield of lactones. At the same time the productive
transformation of active oxygen depends largely on the
intensity of stirring the reaction mixture. Thus, at the
rotation of the mixer with the rate 150–200 rpm the
yield of 6-heptylvalerolactone is 54.0–57.5%, while at
500–600 rpm 67.5–69.3%.
The application of MeOnBrm or H3PO4 on the
activated carbon AG-3 in our experiments promotes
the oxidation of cyclic ketones without the use of
interphase transfer agents, in particular, quaternary
ammonium compounds. The process of oxidative
adsorption of oxygen by the nanoscale particles of the
activated carbon and reductive desorption of them into
The use of tungsten blue (a mixture of W+4, W+5,
and W+6 oxybromides) for the preparation of a mixed
Yield, %
(a)
(b)
Yield, %
100
90
100
90
80
70
60
50
40
30
20
10
0
100
90
80
70
60
50
40
30
20
10
100
90
80
70
60
50
40
30
20
10
80
70
60
50
40
30
20
10
0
1
2
3
4
5
6
7
8
9
1
2
3
4
5
6
7
8
9
τ, h
τ, h
Fig. 2. Dynamics of oxidation of 2-heptylcyclopentanone at different temperatures in the presence of (a) H3PO4: MoOnBrm/C and
(b) H3PO4: WOnBrm/C. Temperature, °C: (1, 5) 40; (2, 6) 50; (3, 7) 60, and (4, 8) 70.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 81 No. 8 2011

1668
ALIMARDANOV et al.
catalytic system (H3PO4 + MoOnBrm + WOnBrm) leads
only to a slight increase in selectivity, from 80.9–83.4
to 84.9%, and in the yield of lactones, from 67.5–69.3
to 70.4%. A detailed study of the dynamics of
oxidation of 2-heptylcyclopentanone in the presence of
phosphomolybdenum and phosphotungsten systems
(Figs. 2a, 2b) showed that in the temperature range
from 40 to 60°C the transfer of active oxygen proceeds
selectively and the non-productive decomposition of
H2O2 does not exceed 5–7%. Oxidation of 2-heptyl-
cyclopentanone runs with a pronounced induction
period. When the catalysts was kept in a solution of
H2O2 before the experiment, the induction period of
the ketone oxidation was significantly reduced. The
main product of the reaction is the corresponding
lactone. The increase in the temperature from 60 to 80°C
leads not only to increase in the rate of non-productive
decomposition of H2O2, but also reduces the substrate
conversion and the process selectivity. Under these
conditions, in the product significantly increased the
content of the products of secondary transformations
of lactones: hydroxyacids and dibasic acids, as well as
oligomers with ester fragments. The proportion of
active oxygen involved in the formation of the peroxo
complex in situ is 50–60% of its stoichiometric
amount.
used the samples of catalysts containing 5.0 to 15 wt %
of Mon+ or Wn+.
Initial alkyl- and cycloalkylcyclopentanones and
-cyclohexanones were synthesized by the free-radical
addition of α-olefins and cyclenes to ketones in the
presence of di-tert-butyl peroxide [27].
The reaction progress was monitored by perman-
ganatometric measurement of the hydrogen peroxide
concentration and by the GLC analysis of the reaction
mixture. Effective separation of source alkylcyclo-
lanones and formed lactones was achieved using poly-
ethylene glycol succinate deposited in the amount of
10 wt % on spherochrom-W as a phase, at the column
temperature 175–180°C (chromatographs Tsvet-100,
lcol = 2 m, dcol = 2 mm), with the flame ionization
detector. Evaporator temperature 280–300°C, carrier
gas nitrogen [P(N2) 0.3–0.5 kg cm–2].
The oxidation of alkylcyclopentanones and -cyclo-
hexanones was performed at a temperature 30–60°C
and a pressure of 0.1 MPa in a glass reactor equipped
with a jacket for temperature control, mechanical stirrer
with a mercury shutter, reflux condenser, and thermo-
meter.
To the reactor was loaded 0.1–0.2 mole of initial
ketone, and 0.1 g of catalyst. While stirring, to the
reaction mixture through a dropping funnel was added
a solution of the adduct of urea with H2O2 in acetic
acid (active oxygen content 30–32%). Molar ratio
ketone: H2O2 = 1:1,5, the feed rate of oxidant 10–
12 g h–1. Stirring was continued for 5–8 h, until
complete consumption of H2O2.
Thus, the optimal yield of lactones was achieved at
a temperature of 50–60°C and the duration of 7–8 h
(Tables 1 and 2).
These lactones are characterized by a pleasant odor,
and some of them can be used as components of food
essences and additives for scenting and flavoring
compositions [25].
The synthesized lactones were isolated from the
reaction mixture by extraction with toluene (4×50 ml).
The combined toluene extracts were treated with 10%
aqueous solution of NaHCO3, the organic layer was
separated and after drying over MgSO4 it was distilled
at atmospheric pressure and then in a vacuum. The
purity and structure of compounds obtained were
determined using GLC, IR, and NMR spectroscopy.
EXPERIMENTAL
Catalysts were prepared by impregnation of
powdered activated carbon of AG-3 grade (Ssp
=
800 m2 g–1), with acetone or alcohol solution of
molybdenum or tungsten blue obtained by the method
developed previously [26]. According to UV, IR, and
ESR analysis, they are mixtures of molybdenum(V)
and molibdenum(VI) oxobromides of the composition
MoOnBrm (where n = 1, 2; m = 2, 3) with a predo-
minance of MoOBr3·2HBr or a mixture of tungsten
oxobromides W+4, W+5, and W+6, their dimeric and
trimeric forms. The samples obtained after evaporation
of the solvent were treated with 85% aqueous solution
of H3PO4 and before use were subjected to heat
treatment at 120–140°C for 4 h. In experiments were
The IR spectra were recorded on a UR-20 spec-
1
trometer in the range of 400 4000 cm–1. The H and
13C NMR spectra were recorded on a Bruker
spectrometer with operating frequency 300 MHz, from
solutions in deuterochloroform using internal reference
(HMDS).
6-Pentylvalerolactone (6-pentyltetrahydropyran-
2-one) (IIIa) was obtained from 15.4 g of 2-pentyl-
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OXIDATION OF THE CYCLOPENTANONE AND CYCLOHEXANONE ALKYL DERIVATIVES
1669
cyclopentanone (Ia). Yield 12.6 g (74%), bp 118–
120ºC (2 mm Hg), d420 0.9723, nD20 1.4590. IR spectrum
d420 0,9646, nD20 1.4620. Found, %: C 71.57, H 10.76.
C11H20O2. Calculated, %: C 71.74, H 10.87.
1
ν, cm–1: 1730 (C=O), 1050 (COC) [28]. H NMR
7-Hexylcaprolactone (7-hexyloxepan-2-one) (IVb)
was obtained from 18.2 g of 2-hexylcyclohexanone
(IIb). Yield 14.4 g (72.6%), bp 150–155°C (2 mm Hg),
d420 0.9540, nD20 1.4630. Found, %: C 72.61, H 11.02.
C12H22O2. Calculated, %: C 72.72, H 11.11.
spectrum, δ, ppm: 1.11 s (3H, CH3), 1.50–1.92 m
(12H, 6CH2), 2.54d (2H, CH2, C = O), 4.45 t (1H CH).
13C NMR spectrum, δ, ppm: 169.5–170.6 (C=O), 79.8–
80.5 (–C–O–C–), 37 and 38.5 (CH2CH2CO), 13.5–
14.2. (CH3), 18.0–31.5 (6CH2) [29]. Found, %: C
70.25, H 10.42. C10H18O2. Calculated, %: C 70.59, H
10.59.
7-Heptylcaprolactone (IVc) was obtained from
19.6 g of 2-heptylcyclohexanone (IIc). Yield 15.1 g
(71,4%), bp 155–160°C (2 mm Hg), d420 0.9462, nD20
1.4642. Found, %: C 73.45, H 11.22. C 13 N 24 O 2.
Calculated,%: C 73.58, H 11.32.
Similar spectral data were obtained for other lacto-
nes, Ib–Ih and IIa–IIh.
6-Hexylvalerolactone (IIIb) was obtained from
16.8 g of 2-hexylcyclopentanone (Ib). Yield 14.3 g
(78%), bp 125–128ºC (2 mm Hg), d420 0.9631, nD20
1.4606. Found, %: C 71.42, H 10.68. C11H20O2.
Calculated, %: C 71.74, H 10.9.
7-Cyclododecylcaprolactone (IVh) was obtained
from 26.4 g of 2-cyclododecylcyclohexanone (IIh).
Yield 19.7 g (70.5%), bp 212–214°C (10 mm Hg), d420
0.8954, nD20 1.4370. Found, %: C 77.02, H 11.35.
C18H32O2. Calculated,%: C 77.14, H 11.43.
6-Heptylvalerolactone (IIIc) was obtained from
18.2 g of 2-heptylcyclopentanone (Ic). Yield 14.9 g
(75.2%), bp 135–140°C (2 mm Hg), d420 0.9585, nD20
1.4622. Found, %: C 72.46, H 10.84. C12H22O2.
Calculated, %: C 72.73, H 11.11.
7-Bicyclo[2.2.1]heptylcaprolactone (7-norbornyl-
oxepan-2-one) (IVg) was obtained from 19.2 g of 2-
bicyclo[2.2.1]heptylcyclohexanone (IIg). Yield 17.1 g
(82.0%), bp 130–132°C (2 mm Hg), d420 1,1307, nD20
1.5330. Found, %: C 74.85, H 15.26. C13H20O2.
Calculated, %: C 75.0, H 15.38.
6-Cyclopentylvalerolactone (IIId) was obtained
from 15.2 g of 2-cyclopentylcyclopentanone (Id).
Yield 12.6 g (74.9%), bp 120–123ºC (3 mm Hg), d420
1.0658, nD20 1.4882. Found, %: C 71.12, H 9.38.
C10H16O2. Calculated, %: C 71.43, H 9.52.
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no. 21, 19R2.27P.
6-Cyclohexylvalerolactone (IIIe) was obtained
from 16.6 g of 2-cyclohexylcyclopentanone (Ie). Yield
12.4 g (68.4%), bp 129–130ºC (2 mm Hg), d420 1.0566,
nD20 1.4928. Found, %: C 75.22, H 9.72. C11H18O2.
Calculated, %: C 75.5, H 9.89.
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6-Bicyclo[2.2.1]heptylvalerolactone (6-norbornyl-
tetrahydropyran-2-one) (IIIg) was obtained from
17.8 g of 2-bicyclo[2.2.1]heptylcyclopentanone (Ig).
Yield 15.5 g (80%), bp 112–114ºC (3 mm Hg), d420
1.1075, nD20 1.5220. Found, %: C 73.95, H 9.12.
C12H18O2. Calculated, %: C 74.23, H 9.28.
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25g of 2-cyclododecylcyclopentanone (Ih). Yield 16.8
g (63%), bp 206–210ºC (10 mm Hg). Found, %: C
76.58, H 11.36. C17H30O2. Calculated, %: C 76.69, H
11.28.
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