ASIAN JOURNAL

OF ORGANIC CHEMISTRY
Accepted Article

Title: An efficient and green synthesis of 1-indanone and 1-tetralone via intramole-
cular Friedel-Crafts acylation reaction

Authors: Thach Ngoc Le

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To be cited as: Asian J. Org. Chem. 10.1002/ajoc.201402274

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Asian Journal of Organic Chemistry 10.1002/ajoc.201402274

FULL PAPER

An efficient and green synthesis of 1-indanone and 1-tetralone via

intramolecular Friedel-Crafts acylation reaction.
Phuong Hoang Tran,[a] Vy Hieu Huynh,[a] Poul Erik Hansen,[b] Duy-Khiem Nguyen Chau,[a] and Thach
Ngoc Le*[a]

Abstract: Metal triflate-catalyzed intramolecular Friedel-Crafts
acylation of 3-arylpropanoic and 4-arylbutanoic acids in triflate anion
ionic liquids under monomode microwave irradiation is reported. The
environmentally benign synthetic procedure allows the formation of
cyclic ketones in good yields within a short reaction time. The
catalytic system metal triflate in triflate anion ionic liquids can be
easily recovered and reused several times without significant loss of
the catalytic performance.
liquids as the most important alternatives to volatile organic
solvents.[30-36] The Friedel–Crafts acylation using metal triflates
in ionic liquids has been studied extensively in recent years. [37-44]
Herein, we reported preliminary results on the intramolecular
Friedel–Crafts acylation using various metal triflates in 1-butyl-3-
methylimidazolium trifluoromethanesulfonate [bmim]OTf and 1-
butylpyridinium trifluoromethanesulfonate [bupy]OTf ionic liquids
under monomode microwave irradiation.

Results and Discussion

Introduction
Two ionic liquids reported in our research, [bmim]OTf and
The intramolecular Friedel–Crafts acylation is a useful method to
[bupy]OTf, were synthesized under monomode microwave
synthesize pharmaceutical products.[1,2] 1-Indanones and 1-
irradiation in a two-step reaction path (Scheme 1). The first step
tetralones are usually obtained by the intramolecular Friedel–
was the direct butylation of 1-methylimidazole and pyridine with
Crafts acylation of 3-arylpropanoyl chloride and 4-arylbutanoyl
butyl bromide and the optimal condition for each starting
chloride, respectively, using strong Lewis acids.[3-5] However,
substrate was determined as follows: 1-methylimidazole (80 oC,
these Lewis acids have to be used in more than stoichiometric
20 min) and pyridine (130 oC, 15 min). In the second step,
amount, and additionally cannot be recycled after the usual
bromide ions were replaced by triflate ions by means of the
aqueous work-up.[2] Besides, the acyl chlorides are not green
anion metathesis using LiOTf as the source of triflate ion. The
acylating agents because their preparation from carboxylic acids
results are shown in Table 1. Compared to those in a previous
generates corrosive by-products such as HCl and SO2.[6]
report,[36,45] this method allowed a fast and facile preparation of
Consequently, the direct Friedel–Crafts cyclization of carboxylic
[bmim]OTf and [bupy]OTf ionic liquids in excellent total yields
acids is preferable to the methods using acyl chlorides due to its
and within a short time. Moreover, it also avoided using excess
short and simple procedure as well as the formation of water as
amounts of reactants and/or organic solvents as reaction media.
a sole non-toxic by-product. However, the use of carboxylic
acids traditionally requires the treatment with an excess of Lewis
acid or Brönsted acid which could not be recovered and
reused.[5,7-10] Metal triflates are efficient and green catalysts for
Friedel-Crafts acylation.[11-22] Recently, metal triflate-catalyzed
Friedel-Crafts acylation using carboxylic acid as acylating
reagent has been studied extensively.[23-27] Although the
intramolecular Friedel–Crafts acylation of carboxylic acids has
been catalyzed by metal triflates with only 5 – 10% catalytic Scheme 1. Synthesis of triflate anion ionic liquids.
loading, the requirement of volatile organic solvents and long
reaction times are current shortcomings.[28,29]
For two decades, much attention has been focused on ionic

[a] Thach Ngoc Le, Phuong Hoang Tran, Vy Hieu Huynh, Duy-Khiem Table 1. Microwave-assisted synthesis of [bmim]OTf and [bupy]OTf.
Nguyen Chau
Department of Organic Chemistry Temperature (oC); Time (min) Isolated
University of Science, VNU-HCM Entry ILs yield
227 Nguyen Van Cu St., Dist. 5, Ho Chi Minh City, Viet nam First step Second step (%)
E-mail: lenthach@yahoo.com
thphuong@hcmus.edu.vn 1 [bmim]OTf 80; 20 80; 10 63
[b] Poul Erik Hansen
Department of Science, Systems and Models 2 [bmim]OTf 80; 20 80; 20 75
Roskilde University
POB 260, Roskilde DK-4000, Denmark 3 [bmim]OTf 80; 20 100; 20 96
E-mail: poulerik@ruc.dk
Asian Journal of Organic Chemistry 10.1002/ajoc.201402274

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4 [bmim]OTf 80; 20 100; 30 79 ranging from 54% to 79%. Control experiments using TfOH
instead of lanthanide triflate have been tested. However, in this
5 [bmim]OTf 80; 20 120; 20 96 method, the yield of 1-tetralone was decreased due to the
formation of the self-aldol condensation by-product of 1-tetralone
6 [bmim]OTf 80; 20 120; 30 90
(Table 2, entries 19, 20).
7 [bupy]OTf 130; 15 130; 10 68 Four metal triflates including Tb(OTf) 3, Tm(OTf)3, Yb(OTf)3 and
Gd(OTf)3 giving good yields (over 80%) were chosen to study of
8 [bupy]OTf 130; 15 130; 15 82
the intramolecular Friedel-Crafts acylation of other substrates.
9 [bupy]OTf 130; 15 130; 20 89 All these metal triflates showed good catalytic activity in Friedel-
Crafts cyclization of 3-phenylpropanoic acid and 3-(3,4-
10 [bupy]OTf 130; 15 130; 30 79 dimethoxyphenyl)propanoic acid in both [bmim]OTf and
[bupy]OTf media.
11 [bupy]OTf 130; 15 150; 20 78
As expected, 1-indanone, which is derived from the five-
12 [bupy]OTf 130; 15 120; 20 83 membered ring cyclization of 3-phenylpropanoic acid, was
obtained in slightly lower yield than 1-tetralone, the homologous
13 [bupy]OTf 130; 15 100; 20 76
six-membered ring ketone (Table 2, entries 21-28). To our
14 [bupy]OTf 130; 15 80; 20 55 delight, the self-aldol condensation by-product of 1-indanone
was not observed in the final product. [29] No product was formed
in the absence of the ionic liquids (Table 2, entry 29). A
significant drop in yield was observed when conventional
The microwave-assisted triflate-catalyzed intramolecular heating (thermostat-controlled oil bath) was used in place of
Friedel–Crafts acylation of 4-phenylbutanoic acid was selected microwave irradiation. However, it can also be seen from Table
as a model reaction to prove the important role of the 2 that the ionic liquid [bmim]OTf showed a better performance
synthesized ionic liquids as green reaction media. Tb(OTf) 3 was as green reaction medium compared with a traditional solvent
chosen as a typical catalyst and used at a loading of 10 mol% to such as C6H5Cl (Table 2, entries 30 and 31).
4-phenylbutanoic acid. After being heated at 220 oC in 30 min, Unlike 3-phenyl propanoic acid, 3-(3,4-
[bmim]OTf and [bupy]OTf-mediated intramolecular Friedel-Crafts dimethoxyphenyl)propanoic acid (3) containing two activating
cyclization afforded the desired product 1-tetralone in excellent methoxy substituents gave nearly the same yield (83% to 91%)
isolated yields (89% and 87%, respectively). All attempts to as 4-phenylbutanoic acid. Interestingly, compared with previous
reduce the reaction time, temperature or the amount of catalyst reports in which the intramolecular acylation of compound (3)
loading led to lower yields. resulted in a mixture of two cyclization isomers, [29] this method
The optimized conditions were then applied to thirteen other showed regioselectivity and gave 5,6-dimethoxy-1-indanone as
metal triflates in order to study their catalytic scope in [bmim]OTf. the only product. This compound was regarded as an important
The results were listed in Table 2. Along with Tb(OTf) 3, three intermediate in a reported synthetic pathway of donepezil
other lanthanide triflates also showed good catalytic hydrochloride (Scheme 2), a drug for treatment of Alzheimer’s
performance with the yield of 1-tetralone exceeding 80% (Table disease.[46-48] Therefore, our research could give a significant
2, entries 5-6, 10-11). The remaining lanthanide triflates such as improvement in producing the first intermediate with absolute
La(OTf)3, Ce(OTf)3, Nd(OTf)3, Pr(OTf)3, Dy(OTf)3, Ho(OTf)3 and regioselectivity and in that manner diminishing the waste
Er(OTf)3 and other metal triflates demonstrated moderate formation. Furthermore, demethylation, which is often observed
catalytic performance with the isolated yield of 1-tetralone for methoxy containing starting materials, is not observed. [49-51]
Asian Journal of Organic Chemistry 10.1002/ajoc.201402274

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a
Table 2. Microwave-assisted intramolecular Friedel-Crafts acylation using metal triflate in triflate anion ionic liquids.

b
Entry Substrate Catalyst Ionic liquids Product Yield (%)

1 La(OTf)3 [bmim]OTf 70
2 Ce(OTf)3 [bmim]OTf 68
3 Nd(OTf)3 [bmim]OTf 67
4 Pr(OTf)3 [bmim]OTf 68
5 Gd(OTf)3 [bmim]OTf 81
6 Tb(OTf)3 [bmim]OTf 89
7 Dy(OTf)3 [bmim]OTf 65
8 Ho(OTf)3 [bmim]OTf 74
9 Er(OTf)3 [bmim]OTf 65
10 Tm(OTf)3 [bmim]OTf 82
11 Yb(OTf)3 [bmim]OTf 83
12 In(OTf)3 [bmim]OTf 79
13 Cu(OTf)2 [bmim]OTf 54
c
14 Bi(OTf)3 [bmim]OTf 72
15 Tb(OTf)3 [bupy]OTf 87
16 Tm(OTf)3 [bupy]OTf 78
17 Yb(OTf)3 [bupy]OTf 84
18 Gd(OTf)3 [bupy]OTf 82
19 TfOH - 42d
20 TfOH [bupy]OTf 50e
21 Tb(OTf)3 [bmim]OTf 82
22 Tm(OTf)3 [bmim]OTf 75
23 Yb(OTf)3 [bmim]OTf 76
24 Gd(OTf)3 [bmim]OTf 74
25 Tb(OTf)3 [bupy]OTf 79
26 Tm(OTf)3 [bupy]OTf 73
27 Yb(OTf)3 [bupy]OTf 70
28 Gd(OTf)3 [bupy]OTf 78
29 Tb(OTf)3 - Tracef
30 Tb(OTf)3 [bupy]OTf 36g
31 Tb(OTf)3 C6H5Cl 20 g
32 Tb(OTf)3 [bmim]OTf 91
33 Tm(OTf)3 [bmim]OTf 85
34 Yb(OTf)3 [bmim]OTf 78
35 Gd(OTf)3 [bmim]OTf 83
36 Tb(OTf)3 [bupy]OTf 88
37 Tm(OTf)3 [bupy]OTf 79
38 Yb(OTf)3 [bupy]OTf 74
39 Gd(OTf)3 [bupy]OTf 80
a
Reaction condition: substrate (1 mmol), metal triflate (0.1 mmol), ionic liquids (0.1 g); control experiment using TfOH: 4-
phenylbutanoic acid (1 mmol), TfOH (1 mmol), [bmim]OTf (0.1 g) or solvent-free. b Isolated yield, the remaining is unreacted
starting material. c Microwave irradiation at 180 oC in 30 min. d Microwave irradiation at 120 oC in 10 min. e Microwave
irradiation at 150 oC in 10 min. f Reaction without ionic liquid. g Conventional heating at 220 oC in 30 min.
Asian Journal of Organic Chemistry
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Scheme 2. Synthesis of donepezil hydrochloride from
dimethoxyphenyl)propanoic acid.
The recyclability of Tb(OTf)3 in [bmim]OTf was confirmed
under microwave irradiation for the intramolecular Friedel-
Crafts acylation of three substrates. Due to its high
dissolubility in the ionic liquid [bmim]OTf, Tb(OTf)3 could be
easily recovered in quantitative yield. After being washed
many times with diethyl ether to remove organic substrates
and products completely, the mixture Tb(OTf) 3/[bmim]OTf
was dried in vacuum at 80 oC in 90 min. For each substrate,
the recycled catalytic mixture Tb(OTf) 3/[bmim]OTf was used
for four consecutive runs at 220 oC in 30 min under
microwave irradiation (Scheme 3). The yield of isolated
product decreased slightly after each run. The process for
recycling Tb(OTf)3 in [bmim]OTf is simple and efficient so it
can be applied on a large scale.
Yields of 4 Yields of 5 Yields of 6
Scheme 3. Recyclability of Tb(OTf)3 in [bmim]OTf under microwave
irradiation at 220 oC in 30 min.
Conclusions
The intramolecular Friedel-Crafts acylation of carboxylic acids
under monomode microwave irradiation using a novel
catalytic system, metal triflates in triflate anion ionic liquids
has been developed. This green method afforded cyclic
ketones in excellent yield within a short time without releasing
any toxic by-products. The recycled catalyst showed nearly
the same performance as the fresh one until the fourth
regeneration cycle.
Experimental Section
General method. All reactions were performed in a CEM Discover
apparatus designed for microwave-assisted synthesis with safe
pressure regulation using a 10 mL pressurized glass vessel with
Teflon-coated septum and a vertically-focused IR temperature sensor
controlling reaction temperature. Flash column chromatography was
10.1002/ajoc.201402274
performed on silica gel from Merck (200-300 mesh). GC–MS analyses
were performed on an Agilent GC System 7890 equipped with a mass
selective detector Agilent 5973N and a capillary column DB-5MS
(length = 30 m, inner diameter = 250 µm, film thickness = 0.25 µm).
The 1H and 13C NMR spectra were recorded on a Bruker Advance
500 MHz spectrometer using CDCl3 as solvent and TMS as internal
3-(3,4- standard. HRESIMS data were recorded on Bruker micrOTOF-QII MS,
8O eV.
Chemicals. The starting materials, celite and metal triflates were
purchased from Sigma-Aldrich and were used without further
purification. Silica gel, magnesium sulfate and sodium carbonate were
purchased from Merck. Ethyl acetate, hexane and diethyl ether were
obtained from Chemsol (Vietnam).
General procedure for the synthesis of triflate ionic liquids. In a
10 mL pressurized glass vessel with Teflon-coated septum, a mixture
of 1-methylimidazole (0.4105 g, 5 mmol) or pyridine (0.3955 g, 5
mmol) and 1-bromobutane (0.6850 g, 5 mmol) was heated under
microwave irradiation at 80 C in 20 min (1-methylimidazole) or at 130
o
C in 15 min (pyridine). Then, LiOTf (0.78 g, 5 mmol) was added and
the resulting mixtures were further heated at 100 C in 20 min (1-
methylimidazole) or at 130 oC in 20 min under microwave activation.
The reaction mixture was cooled to ambient temperature, then the
mixture was diluted with 5 mL of acetonitrile. After filtration through
celite, the solvent was removed. The crude products were washed
with diethyl ether and concentrated by rotary evaporator to obtain
[bmim]OTf (1.3824 g, 96% yield) and [bupy]OTf (1.2683 g, 89% yield).
The purity and authenticity of the synthesized ionic liquids were
confirmed by 1H, 13C NMR spectroscopy and HR-ESI-MS.
1-Butyl-3-methylimidazolium triflate.[36,45] 1H NMR (500 MHz, CDCl3) δ
= 9.00 (s, 1H), 7.37 (s, 1H), 7.34 (s, 1H), 4.14 (t, J = 7.4 Hz, 2H), 3.91
(s, 3H), 1.81 (m, 2H), 1.31 (m, 2H), 0.90 (t, J = 7.4 Hz, 3H). 13C NMR
(125 MHz, CDCl3) δ = 136.6, 123.7, 122.3, 49.8, 36.3, 31.9, 19.3,
13.2. HR-ESI-MS (M-OTf) m/z (%) Calcd. for [C8H15N2]+ : 139.1229,
found: 139.1239. Calcd. for [CF3SO3]-: 148.9514, found: 148.9511.
1-Butylpyridinium triflate.[36,45] 1H NMR (500 MHz, CDCl3) δ = 8.93 (d,
J = 5.6 Hz, 2H), 8.40 (t, J = 7.8 Hz, 1H), 8.00 (m, 2H), 4.67 (t, J = 7.5
Hz, 2H), 1.93 (m, 2H), 1.33 (m, 2H), 0.90 (t, J = 7.4 Hz, 3H). 13C NMR
(125 MHz, CDCl3) δ = 145.8, 144.2, 128.6, 61.8, 32.9, 18.8, 12.8. HR-
ESI-MS (M-OTf) m/z (%) Calcd. for [C9H14N]+ : 136.1126, found:
136.1142. Calcd. for [CF3SO3]-: 148.9514, found: 148.9511.
General procedure for intramolecular Friedel-Crafts acylation. A
10 mL glass vessel was charged with Tb(OTf)3 (0.0606 g, 0.1 mmol),
[bmim]OTf (0.1 g) and 4-phenylbutanoic acid (0.164 g, 1 mmol) and
the reaction mixture was heated at 220 oC in 30 min under microwave
activation. After being cooled, the resulting mixture was extracted by
diethyl ether (3 x 20 mL). The ether layers were combined, washed
with water (10 mL), aqueous Na2CO3 solution (2 x 20 mL), brine (10
mL), and dried over MgSO4. The solvent was then removed by a
rotary evaporator. Pure 1-tetralone was obtained after the purification
by flash chromatography using hexane, then hexane/ethyl acetate
(9:1) as eluents and its isolated yield was up to 89%. The purity and
authenticity of the cyclic ketones were confirmed by GC-MS, 1H and
13
C NMR spectroscopy.
1-Tetralone (4).[8,52] 1H NMR (500 MHz, CDCl3) δ = 8.04 (m, 1H), 7.47
(dt, J = 7.5, 1.4 Hz, 1H), 7.30 (t, J = 7.9 Hz, 1H), 7.25 (m, 1H), 2.97 (t,
J = 6.1 Hz, 2H), 2.66 (m, 2H), 2.14 (m, 2H). 13C NMR (125 MHz,
CDCl3) δ = 198.3, 144.5, 133.3, 132.7, 128.7, 127.2, 126.6, 39.2, 29.7,
23.3. GC-MS (EI, 70 eV) m/z: 146 ([M]+).
1-Indanone (5).[5,10] 1H NMR (500 MHz, CDCl3) δ = 7.77 (d, J = 7.7 Hz,
1H), 7.63 – 7.55 (m, 1H), 7.48 (d, J = 7.7 Hz, 1H), 7.37 (t, J = 7.4 Hz,
1H), 3.15 (m, 2H), 2.70 (m, 2H). 13C NMR (125 MHz, CDCl3) δ =
Asian Journal of Organic Chemistry 10.1002/ajoc.201402274

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