790
Jia-Rong and Guang
compound 3, melted at 119–120◦C. Anal. Calcd.
(%) for C19H16O4S: C, 67.04; H, 4.74; S, 9.42.
Found (%): C, 67.26; H, 4.87; S, 9.07; 1H NMR
(CD3COCD3, ppm): δ = 2.44 (s, 3H), 2.69 (s,
3H), 7.27 (dd, 1H), 7.46 (t, 2H,), 7.66 (d, 1H),
7.78 (d, 2H), 7.95 (d, 1H), 8.05 (dd, 1H), 8.10
(d, 1H), 8.64 (s, 1H). All sorption bands in IR
data of 3 appeared as expected. 1681 cm−1 corre-
Scheme 1.
−1
---
---
sponds to C O, 1594 cm corresponds to C C
--- ---
of naphthalene ring stretching absorption bands,
and 1369 cm−1 corresponds to O S O stretch-
--- ---
--- ---
ing absorption bands. The EI-MS of 3 gave the
molecular ion peaks (340, M) and those of the
main fragments.
funnel. The stirred mixture was heated quickly
to boil and reflux for 2 h. The hot solution was
filtered through a mineral wool plug to remove
the oily residue. The solid, after cooling, was
filtered out through a glass frit. Then the solid
was dissolved in 20 mL of ethyl acetate, washed
with brine, dried over with anhydrous magnesium
sulfate, and the solvent was removed under re-
duced pressure to give a crude product 2 0.74 g
(79.6%). The solid was dissolved in a base solu-
tion, and the diluted HCl was dropped in till white
deposit appeared entirely. The solid was filtered
out to afford pure product, melted at 172.5–174◦C
(Ref. 173.5–177◦C).4 All absorption bands in IR
data of 2 appeared as expected. 3365 cm−1 cor-
Table 1. Crystallographic Data and Structure Refinement for 3
Compound
CH3C6H4SO2OC10H6COCH3
CCDC deposit No.
253163
Chemical formula
Formula weight
Temperature (K)
Crystal size(mm)
Crystal system
C19H16O4S
340.38
293(2)
0.81 × 0.41 × 0.11
Orthorhombic
Pbca
Space group
Unit-cell dimensions
˚
a (A)
12.727(3)
14.560(3)
17.688(4)
3277.8(11)
8
---
responds to OH stretching absorption bands,
˚
b (A)
−1
1660 cm−1 corresponds to C O, and 1630 cm
---
---
˚
c (A)
---
3
corresponds to C C of naphthalene ring stretch-
˚
---
Volume (A )
Z
ing absorption bands. The EI-MS of 2 gave the
molecular ion peaks (186, M) and those of the
main fragments.
Color/shape
Colorless/platelet
1.379
0.217
Density (calcd.) (g/cm3)
Absorption coefficient (mm−1
F(000)
)
1424
Diffractometer/scan
Radiation/wavelength
ω
Synthesis of 2-acetylnaphthalen-6-yl
4-methylbenzosulfonate 3
Mo Kα (graphite
˚
monochrom.) 0.71073 A
2.30 ≤ θ ≤ 27.44
28209
θ range for data collection (◦)
Reflections collected
Independent/observed reflections 3733
Absorption correction
Max. and min. transmission
Refinement method
0.93 g (5 mmol) of 2, 1.00 g (5.24 mmol)
of p-toluenesulfonyl chloride, 10 drops (about
0.5 mL) of triethylamine, and 20 mL of tetrahy-
drofuran were added into a 50 mL three-neck
round bottom flask equipped with a reflux con-
denser. The resulted mixture was heated to re-
flux for 24 h. The solution was filtered out to
remove the indissoluble substance and the filtrate
was evaporated to give 1.23 g (72%) of 3. Re-
crystallization from ethyl acetate to give the title
Empirical
0.9759 and 0.8438
Full-matrix least-squares
on F2
3733/0/217
0.846
R1 = 0.0402, wR2 = 0.0600
R1 = 0.1097, wR2 = 0.0660
0.208, −0.229
Data/restraints/parameters
Goodness of fit on F2
Final R indices [I ≥ 2σ(I)]
R indices (all data)
Largest diff. Peak and
−3
˚
hole (e A
)