An Effective and Environmentally Friendly Synthesis of 1,3-Keto-alcohols

Full text of DOI:10.1080/00304948.2019.1693239

Organic Preparations and Procedures International
The New Journal for Organic Synthesis
ISSN: 0030-4948 (Print) 1945-5453 (Online) Journal homepage: https://www.tandfonline.com/loi/uopp20
An Effective and Environmentally Friendly
Synthesis of 1,3-Keto-alcohols
Tülay Yıldız, Hacer Can & Ayşe S. Yusufoğlu
To cite this article: Tülay Yıldız, Hacer Can & Ayşe S. Yusufoğlu (2020): An Effective and
Environmentally Friendly Synthesis of 1,3-Keto-alcohols, Organic Preparations and Procedures
International, DOI: 10.1080/00304948.2019.1693239
To link to this article: https://doi.org/10.1080/00304948.2019.1693239
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ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
https://doi.org/10.1080/00304948.2019.1693239
EXPERIMENTAL PAPER
An Effective and Environmentally Friendly
Synthesis of 1,3-Keto-alcohols
€
ꢀ
Tulay Yıldız , Hacer Can, and Ays¸e S. Yusufoglu
Department of Chemistry, Istanbul University-Cerrahpasa, Avcilar, Istanbul, Turkey
ARTICLE HISTORY Received 22 January 2019; Accepted 31 August 2019
The 1,3-hydroxycarbonyl group is an essential synthon for natural products and bio-
active organic molecules. In order to obtain this structure, a number of reaction meth-
ods have been developed and, among them, the aldol reaction is one of the most
popular and effective.1–6 Green chemistry methods have contributed greatly to the pro-
gress of aldol reactions in recent years. Harmful effects are reduced by solvent-free cata-
lytic aldol reactions7,8 or catalytic aldol reactions in water,9 supercritical fluids10–12 or
ionic liquids.13,14 The use of catalysts can be made more effective by using heteroge-
neous catalysis,15 synthetic chiral catalysts,16 biocatalysts17,18 and biomimetic
catalysts.19,20
Dimethyl sulfoxide (DMSO), in the presence of a little water, can be used as a polar
aprotic solvent in organocatalyzed asymmetric aldol reactions.21–27 According to the
U.S. Environmental Protection Agency (EPA), DMSO has also been classified as a non-
toxic solvent that poses no human health hazard.28
In this study, our aim was to synthesize new tetralone- and indanone-derived 1,3-
keto-alcohols, which can be used as important prochiral intermediates. In the past, these
1,3-keto-alcohols were only synthesized by the Mukaiyama aldol reaction using silyl
enol ethers instead of ketones.29–33 In contrast, because of the reversibility and the diffi-
culty of controlling the enolate geometry, acid- or base-promoted classical aldol reac-
tions give a complex mixture of products. Thus, when the classical aldol reaction is
used to obtain tetralone or indanone-derived 1,3-keto-alcohols, a-b-unsaturated ketone
derivatives generally occur.
When we tried to prepare the ketones with the classic aldol procedure34 and reagents
we always saw the formation of alkene derivatives. Because of high conjugation, tetra-
lone-derived a-b-unsaturated ketones are very stable, so in the typical classic strongly
acidic or basic environment, the keto-alcohol immediately turns into an alkene by dehy-
dration (Scheme 1).
We thus found a new method by testing different conditions (Table 1).
As seen in Table 1, when NaOH was used as the base, there was no keto-alcohol
product 3a and only the a,b-unsaturated ketone occurred at 25 ꢀC (Entry 1). On the
other hand, when K2CO3 was used as the base at room temperature, we observed 3a as
€
CONTACT Tulay Yıldız
tulayyil@istanbul.edu.tr
Department of Chemistry, Istanbul University-Cerrahpasa, Avcilar,
Istanbul, 34320, Turkey.
Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/uopp.
ß 2020 Taylor & Francis Group, LLC

2
T. YILDIZ ET AL.
O
OH
O
-H2O
R
R
Scheme 1. Dehydration of the 1,3-keto-alcohol and highly conjugated product.
O
OH
O
O
K2CO3/ I2
t-BuOH, 100 o
C
R
R
Yield: 85% 6b (with 3b)
91% 6d (with 3d)
R=3-Me (3b), 4-NO2 (3d)
Scheme 2. The oxidation reaction of keto alcohols.
Table 1. Aldol reaction conditions.a
O
O
OH
O
O
Base
Solvent
3a
1a
2a
3alkene
Entry
Base
Solvent
T (ꢀC)
Time (h)
Yield (%)b (3a)
dr(anti/syn)c (3a)
Yield (%)b (3alkene
)
1
2
3
4
5
6
7
8
9
NaOH
NaOH
NaOH
NaOH
KOH
Na2CO3
K2CO3
K2CO3
K2CO3
K2CO3
MeOH
MeOH
MeOH
DMSO
MeOH
MeOH
MeOH
DMSO
H2O
25
0
ꢁ10
ꢁ10
ꢁ10
25
25
25
25
25
5
5
2
2
2
48
48
48
48
24
0
–
98
71
34
25
75
0
0
0
0
0
25
55
50
10
52
75
80
10
95
52:48
62:38
67:33
63:37
65:35
76:24
70:30
58:42
85:15
10
DMSO-H2O (8:2)
aConditions: 1a (10 mmol), 2a (7.5 mmol), and base (10 eq %) in solvent (2.5 mL) were stirred at the corresponding
temperature.
c
bYield of isolated product. The dr values were determined by HPLC analysis using a chiral column.
the only product with good yield. The solvent mixture DMSO-H2O (8:2) showed the
best result with 95% yield in 24 hours (Entry 10). Also very good diastereoselectivity
was achieved with diasteromeric ratio (dr) 85:15 using K2CO3 and DMSO-H2O (8:2) in
the aldol reaction.
We tried some Lewis acids (FeCl3, CoCl2, ZnCl2 and MnCl2) and organic Brønsted
acids (benzoic acid, trifluoroacetic acid (TFA) and N-triflylphosphoramide (NTPA)) as
catalysts in this reaction and compared these acids with K2CO3. The results are sum-
marized in Table 2 and as seen clearly the other catalysts are not better than K2CO3.
With the best conditions in hand, we prepared 1,3-keto-alcohols using tetralone and
different aldehydes. The new 1,3-keto-alcohols and their yields are given in Table 3. A
number of these compounds are novel, but several have been synthesized before using
the Mukaiyama procedure, including 3a,31–33 3c,35 3d,36 and 3e.29
Table 3 shows that the yields change according to the substituents and their positions.
Yields increased with electron-withdrawing groups such as -NO2 (Entry 4). With strong
electron-donating groups such as –MeO the yields were reduced (Entries 5 and 6).
When the aldehydes were substituted with weak electron-donating groups such as Me,
the yields were good (Entries 2 and 3). While good yields were obtained with phenyl

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
3
Table 2. The effect of different Lewis acid or Brønsted acid in Aldol reaction with tetralone and
benzaldehyde.a,b
O
OH
O
O
Catalyst
DMSO-H2O (8:2)
3a
1a
Catalyst
2a
Entry
Time (h)
Yield (%)c (3a)
dr(anti/syn)d (3a)
1
2
3
4
5
6
7
FeCl3
CoCl2
ZnCl2
MnCl2
Benzoic acid
TFA
48
48
48
48
48
48
48
35
0
0
0
0
0
5
59:41
–
–
–
–
–
NTPA
75:25
aConditions: 1a (10 mmol), 2a (7.5 mmol), and acid (10 eq %) in solvent (2.5 mL) were stirred at 25 ꢀC.
b3alkene was not observed in these experiments.
cYield of isolated product.
dThe dr values were determined by HPLC analysis using a chiral column.
Table 3. Scope of aldehydes for the aldol reaction method with tetralone.a
O
O
OH
O
Ar
K2CO3
Ar
H
DMSO-H2O
(8:2)
1a
2a-2i
3a-3i
Entry
Ar
Aldehyde
Product
Yield (%)b
dr(anti/syn)c
1
2
3
4
5
6
7
8
C6H5
2a
2b
2c
2d
2e
2f
2g
2h
2i
3a
3b
3c
3d
3e
3f
3g
3h
3i
95
96
70
95
60
66
80
55
68
94
91
85:15
81:19
73:27
76:24
62:38
81:19
55:45
80:10
65:35
81:19
79:21
3-MeC6H4
2-MeC6H4
4-NO2C6H4
4-MeOC6H4
2-MeOC6H4
2-Naphthyl
2-Furyl
2-Thienyl
2-FC6H4
2-BrC6H4
9
10
11
2j
2k
3j
3k
aConditions: 1a (10 mmol), 2a-2i (7.5 mmol), and K2CO3 (10 eq %) in DMSO-H2O (8:2) (2.5 mL) were stirred at room
temperature.
bYield of isolated product.
cdr values were determined by HPLC analysis using a chiral column.
and naphthyl as aryl groups (Entries 1 and 7), moderate yields were obtained with the
substrates containing heteroaryl groups such as furyl and thienyl (Entries 8 and 9); that
is, alkene derivatives were also formed in these reactions.
We have also used indanone for our aldol reaction method. The results are shown in
Table 4. The yields are between 45-86%. The best yield was obtained with benzaldehyde
and 4-nitrobenzaldehyde with 87 and 86% yield respectively in the reaction of indanone.
With the exceptions of 4a,33 4d36 and 4e,30 the other indanone derivatives are novel.
We also tried the aldol reaction method with 2-heptanone as an aliphatic ketone
(Tables 5 and 6). Compound 5a37 was previously known, and 5d was synthesized for
the first time in this study.

4
T. YILDIZ ET AL.
Table 4. Scope of aldehydes for the aldol reaction method with indanone.a
O
O
OH
O
Ar
K2CO3
Ar
H
DMSO-H2O
(8:2)
1b
2a-2i
4a-4i
Entry
Ar
Aldehyde
Product
Yield (%)b
dr(anti/syn)c
1
2
3
4
5
6
7
8
C6H5
2a
2b
2c
2d
2e
2f
2g
2h
2i
4a
4b
4c
4d
4e
4f
4g
4h
4i
87
75
69
86
60
45
83
45
62
86
75
81:19
82:18
75:25
78:22
65:35
61:39
83:17
77:13
69:31
78:22
76:24
3-MeC6H4
2-MeC6H4
4-NO2C6H4
4-MeOC6H4
2-MeOC6H4
2-Naphthyl
2-Furyl
2-Thienyl
2-FC6H4
2-BrC6H4
9
10
11
2j
2k
4j
4k
aConditions: 1b (10 mmol), 2a-2i (7.5 mmol), and K2CO3 (10 eq %) in DMSO-H2O (8:2) (2.5 mL) were stirred at room
temperature.
bYield of isolated product.
cdr values were determined by HPLC analysis using a chiral column.
Table 5. Aldol reaction conditions for 2-heptanone and benzaldehyde.a
O
O
OH
O
O
H
C5H11
C5H11
C5H11
1c
2a
5a
5alkene
Entry
Base
Solvent
T(ꢀC)
Time (h)
Yield (%)b (5a)
Yield (%)b (5alkene
)
1
2
3
4
5
6
7
K2CO3 (5 eq %)
K2CO3 (5 eq %)
K2CO3 (10 eq %)
DMSO-H2O (8:2)
DMSO-H2O (8:2)
DMSO-H2O (8:2)
DMSO-H2O (8:2)
MeOH
MeOH
MeOH
25
50
50
50
25
48
4
24
24
24
5
5
25
45
25
0
0
15
25
45
50
66
84
20
75
Na2CO3 (10 eq %)
aq. NaOH (40%, 5 mL)
aq. NaOH (40%, 5 mL)
aq.NaOH (40%, 0.1 mL)
ꢁ10
ꢁ18
2
aConditions: 1c (10 mmol), 2a (7.5 mmol), and base in solvent (2.5 mL) were stirred at the corresponding temperature.
bYield of isolated product.
Table 6. Aldol reaction of 2-heptanone with aromatic aldehydes.a
O
O
OH
O
O
K2CO3
C5H11
Ar
C5H11
1c
Ar
2a, 2d
H
C5H11
Ar
DMSO-H2O
50oC, 24 h
5a, 5d
5aalkene,5dalkene
Entry
Ar
C6H5
4-NO2C6H4
Aldehyde
Product
Yield (%)b Alcohol product
Yield (%)b Alkene product
1
2
2a
2d
5a
5d
45
75
50
23
aConditions: 1c (10 mmol), 2a, 2d (7.5 mmol), and K2CO3 (10% equiv.) in DMSO-H2O (8:2) (2.5 mL) were stirred at 50 ꢀC.
bYield of isolated product.
We further showed our 1,3-keto-alcohols can be oxidized to the related 1,3-diketones.38,39
Compounds 3b and 3d were converted to the corresponding diketones 6b and 6d with
K2CO3/I2 (Scheme 2).40 Compound 6b41 was obtained previously by Claisen condensation
of tetralone and the appropriate aryl methyl ester. The diketone 6d is new.

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
5
In summary, we have prepared some new 1,3-keto-alcohols, using a method that is
consistent with green principles. These materials can be useful as prochiral intermedi-
ates. We hope that their preparation may stimulate further research in the synthesis of
chiral compounds or chiral catalysts.
Experimental section
Chemicals were commercially available from Merck, Acros or Aldrich. All novel pru-
ducts were purified by crystallization or column chromatography and were characterized
1
by IR, H-NMR, 13C-NMR, elemental analysis and GC-MS. The reactions were moni-
tored by TLC using silica gel plates and the products were purified by flash column
chromatography on silica gel (Merck; 230–400 mesh), eluted with hexane-ethyl acetate
1
(v/v 9:1). NMR spectra were recorded at 500 MHz for H and 125 MHz for 13C using
Me4Si as the internal standard in CDCl3. GC-MS spectra were recorded on Shimadzu/
QP2010 Plus. IR spectra were recorded on a Bruker Vertex 70 IR spectrometer. Melting
points were determined with Bu€chi Melting Point B-540 and are uncorrected. For deter-
mination of dr values, HPLC was performed on a Shimadzu/DGU-20A5 HPLC appar-
atus fitted with a 25 cm Chiralcel OD, Chiralcel OD-H, Chiralcel OJ-H and Chiralpac
AD-H chiral columns.
General experimental procedure for aldol reaction
Aromatic aldehyde (7.5 mmol), ketone (10 mmol), K2CO3 (10% equiv.) and 2.5 mL of
DMSO:H2O (8:2) were added to a flask then the mixture was stirred at room temperature
for 1-2 days, as specified by TLC. The reaction was extracted with dichloromethane (3 X
10 mL). Then the combined extracts were washed with saturated brine and dried over
anhydrous Na2SO4; after filtration the solvents were removed under reduced pressure.
Reactions were monitored by thin layer chromatography and visualized by using UV light.
For determination of the isolated yield, flash chromatography was performed on silica gel
(Merck; 230–400 mesh) with hexane-ethyl acetate (v/v 9:1) as the mobile phase.
General procedure for oxidation of keto alcohols
Diketones were synthesized by oxidation of their corresponding 1,3- keto alcohols using
I2/K2CO3 in t-BuOH, according to this procedure: keto-alcohol (0.1 mmol), iodine
(0.2 mmol), K2CO3 (0.2 mmol) and 4 mL of t-BuOH are added to a flask and the mix-
ture refluxed at 100ꢀ C for 16 hours. When the reaction was finished (TLC, hexane-ethyl
acetate (v/v 9:1)), an excess of saturated sodium bisulfite solution was added. Then the
mixture was stirred at room temperature until the color of iodine was gone. Extraction
was then carried out with dichloromethane. The products were purified by column
chromatography on silica gel with hexane-ethyl acetate (v/v 9:1).

6
T. YILDIZ ET AL.
2-(Hydroxy-phenyl-methyl)-3,4-dihydro-2H-naphthalen-1-one (3a)
Colorless oil. IR (neat, cmꢁ1): 3577, 3459, 3024, 2903, 1664, 1655, 1595, 1451, 1223,
1048, 745, 705 cmꢁ1 1H-NMR (CDCl3): d 1.90-1.95 (m, 1H), 2.08-2.17 (m, 1H),
.
2.81–2.85 (m, 1H), 2.89-2.91 (m, 1H), 2.92–2.95 (m, 1H), 4.98 (s, 1H), 5.72 (s, 1H),
7.22–7.24 (d, 1H, J ¼ 8.1 Hz), 7.33-7.42 (m, 6H), 7.47–7.54 (m, 1H), 8.08-8.11 (m, 1H).
13C-NMR (CDCl3): d 22.2, 28.9, 54.7, 71.6, 125.9–133.7 (9C), 141.1–144.4 (3C), 200.0.
MS m/z: 253 (M þ 1), 233, 202, 115, 91.
Anal. Calcd. for C17H16O2: C, 80.93; H, 6.39. Found: C, 80.75; H, 6.51.
2-(Hydroxy-m-tolyl-methyl)-3,4-dihydro-2H-naphthalen-1-one (3b)
Pale orange solid, mp 89.0-90.0 ꢀC. IR (neat, cmꢁ1): 3479, 2963, 2888, 1664, 1598, 1460,
1
1445, 1367, 1313, 1290, 1232, 1154, 1059, 1013, 803, 760, 728 cmꢁ1. H-NMR (CDCl3):
d 1.80–2.06 (m, 2H), 2.27 (s, 3H), 2.66–2.85 (m, 3H), 4.82–4.84 (d, 1H, J ¼ 8.5 Hz), 5.57
(d, 1H J ¼ 2.5 Hz), 6.98-7.41 (m, 7H), 7.96-7.99 (dd, 1H, J1 ¼ 8.0, J2 ¼ 1.5 Hz). 13C-NMR
(CDCl3): d 20.5, 21.2, 27.9, 53.7, 70.5, 123.9–143.3 (12C), 198.9. MS m/z: 265 (M-1),
233, 247, 202, 128.
Anal. Calcd. for C18H18O2: C, 81.17; H, 6.81. Found: C, 80.88; H, 6.96.
2-(Hydroxy-o-tolyl-methyl)-3,4-dihydro-2H-naphthalen-1-one (3c)
Pale orange solid, mp 113-114 ꢀC. IR (neat, cmꢁ1): 3525, 3064, 2957, 2920, 2859, 1676,
1
1598, 1454, 1364, 1290, 1223, 1085, 762, 742 cmꢁ1. H-NMR (CDCl3): d 1.82-1.87 (m,
1H), 2.10–2.19 (dd, 1H, J1 ¼ 5.0 Hz, J2 ¼ 10.0 Hz), 2.23 (s, 3H), 2.44 (d, 1H, J ¼ 3.9 Hz),
2.59–2.63 (ddd, 1H, J1 ¼ 13.3, J2 ¼ 2.0, J3 ¼ 6.7 Hz), 2.75-2.90 (m, 2H), 5.92 (d, 1H,
J ¼ 6.0 Hz), 7.07–7.25 (m, 5H), 7.38-7.44 (m, 1H), 7.50 (d, 1H, J ¼ 7.6 Hz), 8.00 (m, 1H).
13C-NMR (CDCl3): d 17.9, 20.7, 27.9, 51.3, 66.8, 124.7–138.9 (11C), 143.4, 198.7. MS m/z:
265 (M-1), 278, 262, 232, 202, 128, 115, 90.
Anal. Calcd. for C18H18O2: C, 81.17; H, 6.81. Found: C, 80.95; H, 7.05.
2-[Hydroxy-(4-nitro-phenyl)-methyl]-3,4-dihydro-2H-naphthalen-1-one (3d)
Pale brown solid, mp 140.9–141.8 ꢀC. IR (neat, cmꢁ1): 3580, 3447, 3113, 3081, 2931,
1
1670, 1595, 1511, 1344, 1223, 1065, 1013, 858, 748, 705 cmꢁ1. H-NMR (CDCl3): d
1.68–1.73 (m, 1H), 1.99-2.08 (m, 1H), 2.76-3.01 (m, 3H), 5,04 (d, 1H, J ¼ 8.0 Hz), 5.72
(s, 1H), 7.16–7.31 (m, 2H), 7.40–7.53 (m, 3H), 7.97 (d, 1H, J ¼ 7.5 Hz), 8.14–8.16 (m,
2H). 13C-NMR (CDCl3): d 22.1, 28.8, 54.5, 70.9, 123.5–134.3 (10C), 144.2, 149.5, 199.3.
MS m/z: 279 (M-H2O), 278, 262, 248, 232, 202, 115, 90.
Anal. Calcd. for C17H15NO4: C, 68.68; H, 5.09; N, 4.71. Found: C, 68.83; H, 5.25,
N, 4.52.
2-[Hydroxy-(4-methoxy-phenyl)-methyl]-3,4-dihydro-2H-naphthalen-1-one (3e)
Pale yellow solid, Mp 124.0–125.0 ꢀC. IR (neat, cmꢁ1): 3441, 2966, 2911, 2842, 1678, 1598,
1511, 1457, 1304, 1246, 1220, 1171, 1085, 1030, 797, 768, 742, 662 cmꢁ1. 1H-NMR (CDCl3):

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
7
d 1.93-1.98 (m, 1H), 2.05–2.14 (m, 1H), 2.79-2.84 (m, 1H), 2.91–2.96 (m, 2H), 3.83 (s, 3H),
5.62 (s, 1H), 6.91-6.94 (m, 2H), 7.23–7.24 (d, 1H, J ¼ 7.6 Hz), 7.28–7.36 (m, 4H), 7.43–7.52
(m, 1H), 8.07–8.09 (m, 1H). 13C-NMR (CDCl3): d 22.5, 29.0, 54.6, 55.2, 71.5, 113.6-134.0
(10C), 144.4, 158.71, 200.26. MS m/z: 282 (M), 281, 263, 249, 233, 121, 90.
Anal. Calcd. for C18H18O3: C, 76.57; H, 6.43. Found: C, 76.73; H, 6.24.
2-[Hydroxy-(2-methoxy-phenyl)-methyl]-3,4-dihydro-2H-naphthalen-1-one (3f)
Beige solid, mp 162–163 ꢀC. IR (neat, cmꢁ1): 3482, 3070, 3032, 2978, 2937, 2865, 2839,
1676, 1598, 1488, 1454, 1439, 1362, 1290, 1223, 1051, 1025, 1002, 970, 742, 725,
1
656 cmꢁ1. H-NMR (CDCl3): d 1.73–2.09 (m, 2H), 2.75–2.87 (m, 3H), 2.88–2.92 (dd,
1H, J1 ¼ 15.0 Hz, J2 ¼ 10.0 Hz), 3.70 (s, 3H), 5.90 (s, 1H), 6.77–7.45 (m, 7H), 8.1 (d, 1H,
J ¼ 10.0 Hz). 13C-NMR (CDCl3): d 21.2, 27.9, 51.1, 54.1, 65.6, 108.9, 119.3, 125.4–132.3
(8C), 143.4, 154.4, 199.3. MS m/z: 282 (M), 233, 202, 115, 90.
Anal. Calcd. for C18H18O3: C, 76.57; H, 6.43. Found: C, 76.82; H, 6.36.
2-(Hydroxy-naphthalen-2-yl-methyl)-3,4-dihydro-2H-naphthalen-1-one (3g)
Yellow solid, mp 146–148 ꢀC. IR (neat, cmꢁ1): 3490, 2960, 2920, 1661, 1601, 1454, 1359,
1
1264, 1226, 1091, 1016, 869, 803, 751, 734, 676, 656 cmꢁ1. H-NMR (CDCl3): d 1.52–2.07
(m, 2H), 2.71-2.79 (m, 3H), 4.94 (s, 1H), 5.04 (d, 1H, J ¼ 8.5 Hz), 7.07 (d, 1H, J ¼ 7.5 Hz),
7.18–7.24 (m, 1H), 7.32–7.39 (m, 4H), 7.71–7.78 (m, 4H), 7.99 (d, 1H, J ¼ 8.0 Hz). 13C-
NMR (CDCl3): d 25.2, 27.9, 52.8, 74.6, 123.0–133.0 (16C), 201.3. MS m/z: 284 (M-H2O),
267, 252, 239, 141, 128, 90.
Anal. Calcd. for C21H18O2: C, 83.42; H, 6.00. Found: C, 83.63; H, 6.25.
2-(Furan-2-yl-hydroxy-methyl)-3,4-dihydro-2H-naphthalen-1-one (3h)
Brown oil. IR (neat, cmꢁ1): 3430, 3122, 2937, 2900, 2877, 1670, 1601, 1511, 1454, 1362,
1
1324, 1295, 1226, 1148, 1123, 1099, 1062, 1007, 955, 918, 809, 774, 739, 665 cmꢁ1. H-
NMR (CDCl3): d 1.64–1.70 (m, 1H), 1.95-2.01 (m, 1H), 2.85–2.99 (m, 3H), 3.54 (br s,
1H), 5.33 (d, 1H, J ¼ 2.5 Hz), 6.22–6.27 (m, 2H), 7.13–7.26 (m, 3H), 7.33–7.43 (m, 1H),
7.96 (d, 1H, J ¼ 8.0 Hz). 13C-NMR (CDCl3): d 23.9, 28.9, 51.9, 67.8, 106.9, 110.3,
126.6–134.1 (5C), 141.6, 144.3, 155.08, 199.7. MS m/z: 224 (M-H2O), 206, 195, 170, 165,
152, 128, 118, 90, 81, 63, 51.
Anal. Calcd. for C15H14O3: C, 74.36; H, 5.82. Found: C, 74.56; H, 6.14.
2-(Hydroxy-thiophen-2-yl-methyl)-3,4-dihydro-2H-naphthalen-1-one (3i)
Green oil. IR (neat, cmꢁ1): 3433, 3067, 2929, 2871, 1667, 1601, 1454, 1356, 1226, 1157,
1
1030, 912, 826, 702 cmꢁ1. H-NMR (CDCl3): d 1.61–1.79 (m, 1H), 1.95–2.03 (m, 1H),
2.68–2.91 (m, 3H), 4.93 (s, 1H), 5.2 (s, 1H), 6.88–6.93 (m, 2H), 7.13–7.26 (m, 3H),
7.38–7.43 (m, 1H), 7.98 (d, 1H, J ¼ 8.0 Hz). 13C-NMR (CDCl3): d 25.0, 27.7, 53.4, 70.4,
123.3–133.0 (9C), 143.4, 200.5. MS m/z: 256 (M-2), 207, 193, 147, 118, 103, 90, 82,
43, 41.

8
T. YILDIZ ET AL.
Anal. Calcd. for C15H14O2S: C, 69.74; H, 5.46; S, 12.41. Found: C, 69.88; H, 5.57;
S, 12.23.
2-[(2-Fluoro-phenyl)-hydroxy-methyl]-3,4-dihydro-2H-naphthalen-1-one (3j)
Beige solid, mp 98.4-99.8 ꢀC. IR (neat, cmꢁ1): 3442, 3057, 2949, 2914, 1672, 1598, 1481,
1
1369, 1224, 1174, 1055, 871, 794, 767, 659 cmꢁ1. H-NMR (CDCl3): d 1.88–1.91 (m,
1H), 2.04–2.18 (m, 1H), 2.92–3.00 (m, 4H), 5.98 (d, 1H, J ¼ 4.0 Hz), 7.00–7.07 (m, 1H),
7.16–7.35 (m, 4H), 7.48 (ddd, 1H, J1 ¼ J2 ¼ 12.0 Hz, J3 ¼ 2.0 Hz), 7.62 (ddd, 1H,
J1 ¼ J2 ¼ 13.0 Hz, J3 ¼ 3.5 Hz), 8.07 (dd, 1H, J1 ¼ 13.0 Hz, J2 ¼ 2.0 Hz). 13C-NMR
(CDCl3): d 22.4, 28.9, 52.9, 66.0, 114.8, 115.1, 124.0-133.6 (7C), 144.3, 157.4, 160.7,
199.8. MS m/z: 269 (M-1), 234, 208, 193, 147, 118, 103, 90, 82, 43, 41.
Anal. Calcd. for C17H15FO2: C, 75.54; H, 5.59. Found: C, 75.79; H, 5.52.
2-[(2-Bromo-phenyl)-hydroxy-methyl]-3,4-dihydro-2H-naphthalen-1-one (3k)
White solid, mp 138.2–141.9 ꢀC. IR (neat, cmꢁ1): 3446, 3057, 2951, 2914, 1674, 1598,
1
1454, 1363, 1222, 1128, 1089, 923, 748, 732, 655 cmꢁ1. H-NMR (CDCl3): d 1.75–1.83
(m, 1H), 2.11–2.25 (m, 1H), 2.70 (br s, 1H), 2.90-2.95 (m, 2H), 3.05-3.11 (ddd, 1H,
J1 ¼ 23.0 Hz, J2 ¼ 7.0 Hz, J3 ¼ 4.0 Hz), 6.06 (d, 1H, J ¼ 3.5 Hz), 7.15–7.51 (m, 5H), 7.55
(dd, 1H, J1 ¼ 13.5 Hz, J2 ¼ 2.0 Hz), 7.65 (dd, 1H, J1 ¼ 13.0 Hz, J2 ¼ 3.0 Hz), 8.10 (dd, 1H,
J1 ¼ 13.0 Hz, J2 ¼ 1.0 Hz). 13C-NMR (CDCl3): d 25.9, 28.9, 51.6, 70.2, 121.1, 126.6–136.9
(9C), 140.7, 144.3, 199.5. MS m/z: 329 (M-1), 236, 207, 193, 147, 118, 103, 90, 82,
43, 41.
Anal. Calcd. for C17H15BrO2: C, 61.65; H, 4.56. Found: C, 61.72; H, 4.67.
2-(Hydroxy-phenyl-methyl)-indan-1-one (4a)
Beige solid, mp 156–157 ꢀC. IR (neat, cmꢁ1): 3064, 3029, 2906, 1699, 1604, 1462, 1275,
1
1203, 1094, 999, 843, 751, 711 cmꢁ1. H-NMR (CDCl3): d 1.63 (br s, 1H), 2.93 (dd, 1H,
J1 ¼ 4.0, J2 ¼ 17.0 Hz), 3.38 (dd, 1H, J1 ¼ 8.0, J2 ¼ 17.0 Hz), 3.68 (ddd, 1H, J1 ¼ 4.0,
J2 ¼ J3 ¼ 8.0 Hz), 5.32 (d, 1H, J ¼ 8.0 Hz), 7.19–7.39 (m, 7H), 7.50–7.56 (m, 1H), 7.71 (d,
1H, J ¼ 7.5 Hz). 13C-NMR (CDCl3): d 31.0, 48.8, 70.1, 123.8–141.3 (11C), 153.4, 207.4.
MS m/z: 220 (M-H2O), 191, 165, 132, 155, 104, 91, 77.
Anal. Calcd. for C16H14O2: C, 80.65; H, 5.92. Found: C, 80.45; H, 6.16.
2-(Hydroxy-m-tolyl-methyl)-indan-1-one (4b)
0
White solid, mp 117–118 C. IR (neat, cmꢁ1): 2920, 2850, 1696, 1626, 1603, 1473, 1301,
1
1268, 1238, 1091, 964, 930, 892, 777, 737, 690, 673 cmꢁ1. H-NMR (CDCl3): d 3.25 (s,
1H), 4.36 (s, 5H), 4.86–4.95 (m, 1H), 5.24-5.28 (m, 1H), 9.07–9.79 (m, 8H). 13C-NMR
(CDCl3): d 20.5, 25.6, 53.8, 70.8, 121.5–141.7 (11C), 153.8, 206.3. MS m/z: 253 (M þ 1),
233, 219, 191, 165, 115, 89.
Anal. Calcd. for C17H16O2: C, 80.93; H, 6.39. Found: C, 81.12; H, 6.47.

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
9
2-(Hydroxy-o-tolyl-methyl)-indan-1-one (4c)
0
Beige solid, mp 205.3–206.4 C. IR (neat, cmꢁ1): 3523, 2920, 2851, 1699, 1604, 1468,
1
1261, 1099, 1016, 803, 748, 667 cmꢁ1. H-NMR (CDCl3): d 2.27 (s, 3H), 2.57 (d, 1H,
J ¼ 5.5 Hz), 2.78–2.87 (m, 1H), 2.91–2.98 (m, 1H), 3.18 (dd, 1H, J1 ¼ 17.0 Hz,
J2 ¼ 4.5 Hz), 5.46 (br s, 1H), 7.01 (d, 1H, J ¼ 7.0 Hz), 7.11–7.34 (m, 5H), 7.45–7.52 (m,
1H), 7.65 (d, 1H, J ¼ 8.0 Hz). 13C-NMR (CDCl3): d 25.6, 28.9, 53.8, 70.8, 121.5–141.7
(11C), 153.8, 206.3. MS m/z: 252 (M), 244, 132, 103, 77.
Anal. Calcd. for C17H16O2: C, 80.93; H, 6.39. Found: C, 81.18; H, 6.43.
2-[Hydroxy-(4-nitro-phenyl)-methyl]-indan-1-one (4d)
Orange solid, mp 175–176 ꢀC. IR (neat, cmꢁ1): 3375, 3110, 3078, 2880, 1693, 1601,
1
1509, 1341, 1290, 1206, 1088, 797, 754, 705, 673 cmꢁ1. H-NMR (CDCl3): d 2.61 (d, 1H,
J ¼ 4.5 Hz), 2.78 (dd, 1H, J1 ¼ 8.0 Hz, J2 ¼ 17.0 Hz), 2.98–3.01 (m, 1H), 3.09 (dd, 1H,
J1 ¼ 4.5 Hz, J2 ¼ 17 Hz), 4.02 (d, 1H, J ¼ 1.5 Hz), 5.63 (t, 1H, J ¼ 3.5 Hz), 7.28–7.41 (m,
2H), 7.68 (d, 1H, J ¼ 8.5 Hz), 7.73 (d, 1H, J ¼ 8.5 Hz), 8.16 (d, 2H, J ¼ 8.5 Hz), 8.23 (d,
1H, J ¼ 8.5 Hz). 13C-NMR (CDCl3): d 31.3, 53.5, 54.2, 70.1, 122.6–146.3 (6C), 146.7,
148.3, 148.9, 153.3, 192.6, 205.3. MS m/z: 282 (M-1), 281, 264, 248, 218, 189, 178, 165,
115, 89, 82, 63, 51.
Anal. Calcd. for C16H13NO4: C, 67.84; H, 4.63; N, 4.94. Found: C, 67.64; H, 4.75,
N, 4.71.
2-[Hydroxy-(4-methoxy-phenyl)-methyl]-indan-1-one (4e)
Yellow oil. IR (neat, cmꢁ1): 3433, 2917, 2839, 1690, 1604, 1514, 1468, 1246, 1171, 1030,
832, 751 cmꢁ1
.
1H-NMR (CDCl3): d 1.63 (br s, 1H), 2.96 (dd, 1H, J1 ¼ 17.0, Hz,
J2 ¼ 17.0 Hz), 3.04–3.09 (m, 1H), 3.84 (s, 3H), 4.76 (d, 1H, J ¼ 10.0 Hz), 5.55 (s, 1H),
6.93 (dd, 2H, J1 ¼ 3.0, Hz, J2 ¼ 8.5 Hz), 7.36–7.46 (m, 4H), 7.57–7.63 (m, 1H), 7.80 (dd,
1H, J1 ¼ 11.0, Hz, J2 ¼ 11.0 Hz). 13C-NMR (CDCl3): d 30.0, 54.7, 55.3, 71.9, 113.8, 113.9,
123.8–135.4 (8C), 154.7, 158.9, 209.8. MS m/z: 267 (M-1), 250, 235, 219, 207, 178, 152,
89, 76, 63, 51.
Anal. Calcd. for C17H16O3: C, 76.10; H, 6.01. Found: C, 76.27; H, 6.18.
2-[Hydroxy-(2-methoxy-phenyl)-methyl]-indan-1-one (4f)
Beige solid, mp 150.4–151.7 ꢀC. IR (neat, cmꢁ1): 3548, 2929, 2911, 2839, 1704, 1687,
1
1598, 1460, 1241, 1148, 1085, 1022, 964, 751 cmꢁ1. H-NMR (CDCl3): d 1.50 (br s, 1H),
2.74–2.84 (m, 1H), 3.15–3.20 (m, 2H), 3.79 (s, 3H), 5.75 (s, 1H), 6.82 (d, 1H,
J ¼ 8.5 Hz), 6.95 (dd, 1H, J1 ¼ J2 ¼ 7.5 Hz), 7.19-7.36 (m, 3H), 7.43-7.50 (m, 2H), 7.71
(d, 1H, J ¼ 8.0). 13C-NMR (CDCl3): d 26.1, 51.2, 54.2, 66.9, 109.1, 119.5–136.3 (9C),
153.8, 154.8, 206.5. MS m/z: 267 (M-1), 282, 253, 249, 207, 193, 147, 119, 103, 96, 73,
59, 45.
Anal. Calcd. for C17H16O3: C, 76.10; H, 6.01. Found: C, 76.34; H, 6.22.

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T. YILDIZ ET AL.
2-(Hydroxy-naphthalen-2-yl-methyl)-indan-1-one (4g)
Orange solid, mp 40.0–40.5 ꢀC. IR (neat, cmꢁ1): 3587, 3052, 2923, 1701, 1606, 1468,
1
1278, 1059, 909, 817, 754, 662 cmꢁ1. H-NMR (CDCl3): d 1.57 (s, 1H), 2.70–2.79 (m,
2H), 5.03 (d, 1H, J ¼ 8.8 Hz), 5.76 (s, 1H), 7.07 (d, 1H, J ¼ 7.5 Hz), 7.18–7.24 (m, 1H),
7.32–7.39 (m, 4H), 7.71–7.78 (m, 4H), 7.99 (dd, 1H, J1 ¼ J2 ¼ 7.5 Hz). 13C-NMR
(CDCl3): d 27.7, 52.8, 74.6, 123.0-138.4 (15C), 143.3, 201.3. MS m/z: 270 (M-H2O), 252,
239, 226, 215, 207, 195, 177, 120, 82, 65, 50, 40.
Anal. Calcd. for C20H16O2: C, 83.31; H, 5.59. Found: C, 83.26; H, 5.61.
2-(Furan-2-yl-hydroxy-methyl)-indan-1-one (4h)
Brown oil. IR (neat, cmꢁ1): 3625, 2955, 2920, 2851, 1704, 1627, 1606, 1471, 1385, 1258,
1
1108, 1022, 737 cmꢁ1. H-NMR (CDCl3): d 2.88–2.98 (m, 3H), 3.54 (br s, 1H), 5.33 (d,
1H, J ¼ 2.5 Hz), 6.22 (d, 1H, J ¼ 3.5 Hz), 6.24-6.27 (m, 1H), 7.15 (d, 1H, J ¼ 7.5 Hz),
7.21–7.26 (m, 2H), 7.38–7.42 (m, 1H), 7.97 (dd, 1H, J1 ¼ 8.0 Hz, J2 ¼ 1.0 Hz). 13C-NMR
(CDCl3): d 29.9, 51.9, 67.8, 106.9, 110.2, 126.6–144.3 (7C), 155. 0, 199.7. MS m/z: 210
(M-H2O), 284, 253, 210, 192, 148, 133, 119, 105, 92, 78, 64, 42.
Anal. Calcd. for C14H12O3: C, 73.67; H, 5.30. Found: C, 73.86; H, 5.14.
2-(Hydroxy-thiophen-2-yl-methyl)-indan-1-one (4i)
Green oil, IR (neat, cmꢁ1): 3389, 3070, 2920, 2851, 1687, 1604, 1471, 1428, 1295, 1203,
1
1151, 1097, 1019, 958, 938, 754, 713, 656 cmꢁ1. H-NMR (CDCl3): d 1.67 (br s, 1H),
3.10–3.19 (m, 3H), 3.36 (dd, 1H, J1 ¼ 12.5 Hz, J2 ¼ 9.0 Hz), 5.79 (d, 1H, J ¼ 4.5 Hz),
6.98-7.06 (m, 2H), 7.27 (dd, 1H, J1 ¼ 1.0 Hz, J2 ¼ 5.5 Hz), 7.36–7.64 (m, 2H), 7.78 (d,
1H, J ¼ 7.5 Hz). 13C-NMR (CDCl3): d 27.4, 54.4, 69.2, 123.8–127.4 (6C), 135.1, 136.9,
146.4, 154.7, 206.8. MS m/z: 226 (M-H2O), 197, 165, 152, 89, 76, 63, 51.
Anal. Calcd. for C14H12O2S: C, 68.83; H, 4.95; S, 13.12. Found: C, 68.97; H, 5.16;
S, 13.08.
2-[(2-Fluoro-phenyl)-hydroxy-methyl]-indan-1-one (4j)
Beige solid, mp 149.5–151.5 ꢀC. IR (neat, cmꢁ1): 3456, 3056, 2943, 1689, 1620, 1483,
1
1454, 1228, 1101, 1055, 977, 748, 732, 678 cmꢁ1. H-NMR (CDCl3): d 1.80 (br s, 1H),
4.07–4.21 (m, 1H), 4.96 (d, 1H, J ¼ 2.0 Hz), 5.08 (d, 1H, J ¼ 7.5 Hz), 5.50 (d, 1H,
J ¼ 8.0 Hz), 7.10-7.21 (m, 2H), 7.27–7.49 (m, 4H), 7.70–7.83 (m, 1H), 7.98–7.92 (m,
1H). 13C-NMR (CDCl3): d 30.7, 47.5, 67.5, 111.4, 111.5, 123.9-139.0 (7C), 148.4, 159.7,
161.0, 193.5. MS m/z: 238 (M-H2O), 222, 197, 165, 152, 89, 76, 63,51.
Anal. Calcd. for C16H13FO2: C, 74.99; H, 5.11. Found: C, 74.77; H, 5.35.
2-[(2-Bromo-phenyl)-hydroxy-methyl]-indan-1-one (4k)
Pale yellow solid, mp 180.1–182.7 ꢀC. IR (neat, cmꢁ1): 3396, 3086, 2951, 1687, 1645,
1
1465, 1307, 1298, 1249, 1095, 1058, 1022, 970, 748, 734 cmꢁ1. H-NMR (CDCl3): d 4.85
(br s, 1H), 5.16 (d, 1H, J ¼ 4.0 Hz), 5.29 (d, 1H, J ¼ 3.0 Hz), 5.37 (d, 1H, J ¼ 3.0 Hz),

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
11
6.16 (d, 1H, J ¼ 12.5 Hz), 7.02–7.74 (m, 7H), 7.92-7.96 (m, 1H). 13C-NMR (CDCl3): d
45.2, 72.2, 75.3, 121.0–136.5 (10C), 148.2, 151.2, 193.7. MS m/z: 298 (M-H2O), 222, 197,
165, 152, 89, 76, 63, 51.
Anal. Calcd. for C16H13BrO2: C, 60.59; H, 4.13. Found: C, 60.71; H, 4.22.
1-Hydroxy-1-phenyl-octan-3-one (5a)
Colorless oil. IR (neat, cmꢁ1): 3470, 2933, 2885, 1699, 1607, 1451, 1307, 1235, 763,
1
742 cmꢁ1. H-NMR (CDCl3): d 0.80 (t, 3H, J ¼ 7.0 Hz), 1.13-1.27 (m, 5H), 1.46–1.52
(m, 2H), 2.33 (t, 2H, J ¼ 7.5 Hz), 2.67 (dd, 1H, J1 ¼ 3.0 Hz, J2 ¼ 14.0 Hz), 2.77 (dd, 1H,
J1 ¼ 9.0 Hz, J2 ¼ 17.5 Hz), 5.05 (dd, 1H, J1 ¼ 3.0 Hz, J2 ¼ 9.5 Hz), 7.16–7.20 (m, 1H),
7.25–7.26 (m, 4H). 13C-NMR (CDCl3): d 14.0, 22.9, 25.4, 30.8, 42.6, 51.7, 73.7, 126.7,
126.7, 128.2, 128.2, 128.3, 143.8, 209.7. MS m/z: (M) 220, 202, 187, 173, 149, 131, 105,
77, 58.
Anal. Calcd. for C14H20O2: C, 76.33; H, 9.15. Found: C, 76.54; H, 9.25.
1-Hydroxy-1-(4-nitro-phenyl)-octan-3-one (5d)
Pale yellow oil. IR (neat, cmꢁ1): 3338, 2923, 2853, 1615, 1515, 1469, 1384, 1307, 1253,
1
1176, 1038, 969, 746 cmꢁ1. H-NMR (CDCl3): d 0.82 (t, 3H, J ¼ 7.0 Hz), 1.15–1.25 (m,
4H), 1.49-1.55 (m, 2H), 2.37 (t, 2H, J ¼ 7.0 Hz), 2.73–2.76 (m, 2H), 3.56 (brs, 1H), 5.19
(dd, 1H, J1 ¼ 4.0 Hz, J2 ¼ 8.5 Hz), 7.46 (d, 2H, J ¼ 8.5 Hz), 8.14 (d, 2H, J ¼ 9.0 Hz). 13C-
NMR (CDCl3): d 14.0, 22.5, 23.4, 31.4, 43.8, 50.4, 69.2, 123.8, 124.0, 126.5, 126.7, 147.5,
150.3, 211.3. MS m/z: (M-1) 254, 247, 208, 195, 153, 141, 127, 113, 101, 87, 77, 63, 51.
Anal. Calcd. for C14H19NO4: C, 63.38; H, 7.22; N, 5.28. Found: C, 63.51; H, 7.36;
N, 5.09.
2-(3-Methyl-benzoyl)-3,4-dihydro-2H-naphthalen-1-one (6b)
Pale orange oil. IR (neat, cmꢁ1): 2985, 2930, 2861, 1726, 1682, 1608, 1528, 1469, 1313,
1208, 1116, 865, 753, 718, 683, 627 cmꢁ1 1H-NMR (CDCl3): d 1.89 (ddd, 1H,
.
J1 ¼ 13.5 Hz, J2 ¼ 8.5 Hz, J3 ¼ 4.5 Hz), 2.49-2.43 (m, 1H), 2.39 (s, 2H), 2.84 (dd, 2H,
J1 ¼ 3.5 Hz, J2 ¼ 1.5 Hz), 4.34 (t, 1H, J ¼ 1.5 Hz), 7.18-7.21 (m, 3H), 7.24–7.31 (m, 2H),
7.37 (dd, 1H, J1 ¼ J2 ¼ 8.5 Hz), 7.52 (ddd, 1H, J1 ¼ 7.5 Hz, J2 ¼ 1.5 Hz, J3 ¼ 15 Hz), 8.13
(dd, 2H, J1 ¼ 8.0 Hz, J2 ¼ 1.5 Hz). 13C-NMR (CDCl3): d 21.3, 25.3, 27.0, 64.2, 123.7,
126.9, 127.2, 128.2, 128.7, 128.8, 129.1, 132.7, 134.0, 134.2, 138.0, 143.3, 193.6, 197.9.
MS m/z: (M) 264, 247, 233, 221, 203, 193, 178, 131, 119, 115, 103, 91, 78.
Anal. Calcd. for C18H16O2: C, 81.79; H, 6.10. Found: C, 81.63; H, 6.27.
2-(4-Nitro-benzoyl)-3,4-dihydro-2H-naphthalen-1-one (6d)
Pale brown oil. IR (neat, cmꢁ1): 2955, 2920, 2854, 1727, 1696, 1601, 1517, 1462, 1347,
1
1301, 1232, 1108, 875, 751, 739, 713, 693, 665 cmꢁ1. H-NMR (CDCl3): d 1.69–1.74 (m,
1H), 2.34–2.40 (m, 1H), 2.70-2.86 (m, 2H), 4.40 (t, 1H, J ¼ 1.0 Hz), 7.17 (d, 1H,
J ¼ 10.0 Hz), 7.37 (t, 1H, J ¼ 8.5 Hz), 7.46–7.51 (m, 3H), 8,04 (d, 1H, J ¼ 9.5 Hz), 8.19 (d,

12
T. YILDIZ ET AL.
2H, J ¼ 8.5 Hz). 13C-NMR (CDCl3): d 25.2, 28.0, 29.3, 123.9, 123.9, 127.2, 128.8–129.0
(4C), 134.5, 135.7, 141.6, 142.7, 149.3, 191.9, 196.7. MS m/z: 295 (M), 269, 265, 208,
192, 178, 145, 131, 115, 103, 90, 63, 51.
Anal. Calcd. for C17H13NO4: C, 69.15; H, 4.44; N, 7.74. Found: C, 69.36; H, 4.52;
N, 7.56.
Acknowledgments
This study was supported in a Turkey Scientific and Technological Research Center Project
€ _
(TUBITAK) with project number 214Z234. Also we thank DEVA Holding A.S¸. company for
some NMR and IR analysis.
ORCID
Tu€lay Yıldız
http://orcid.org/0000-0001-5857-2480
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