Microwave-assisted intermolecular aldol condensation: Efficient one-step synthesis of 3-acetyl isocoumarin and optimization of different reaction conditions.
Microwave-assisted intermolecular aldol condensation: Efficient one-step synthesis of 3-acetyl isocoumarin and optimization of different reaction conditions Murat Kocaa,*, Ali S. Ertürkb,*, Adil Umazc a
Department of Pharmacy and Pharmaceutical Technology, Faculty of Pharmacy, 02040, Adıyaman, Turkey
b
Department of Metallurgy and Material Engineering, Faculty of Engineering, Adıyaman University, 02040, Adıyaman, Turkey
c
Department of Chemistry, Faculty of Art and Sciences, Adıyaman University, 02040, Adıyaman, Turkey
SUPPORTING INFORMATION
1
Table of Contents Spectral and analytical Data ......................................................................................................... 3 IR (ATR), 1H NMR, 13C NMR, GC-MS spectra for compound 3 ............................................. 4
2
Spectral and analytical Data 3-acetyl isocoumarin (3):
O 8 7
1 8a
O 2
6
4a 5
3 4
CH3 9
10
O 1
H NMR (500 MHz, CDCl3): δ = 2.56 (s, 3 H, -CH3), 7.37 (s, 1 H, H-4), 7.60~7.68 (m, 2 H, H-5,
H-7), 7.74~7.82 (td, J=7.6, 1.3 Hz, 1 H, H-6), 8.3 (d, J=7.9 Hz, 1 H, H-8); 13
C NMR (400 MHz, CDCl3): δ= 26.1 (C-10), 109.0 (C-4), 122.8 (C-8a), 128.3 (C-8), 130.0 (C-
5), 130.8 (C-7), 135.0 (C-6), 135.3 (C-4a), 148.9 (C-3), 160.9 (C-1), 192.2 (C-9). GC-MS: m/z= 188.10 (M+, %89), 145,1 (100), 117.1 (29), 89,1 (95), 63,1 (16). Melting Point: 130 ± 0.1 oC
3
IR (ATR), 1H NMR, 13C NMR, GC-MS spectra for compound 3 95,1 90 85 80 75 70 65
%T
60 55 50 45 40 35 30
26,0 4000,0
3600
3200
2800
2400
2000
1800 cm-1
1600
1400
Figure S1. IR (ATR) spectrum of compound 3.
4
1200
1000
800
650,0
O 8
1
7
8a
6
4a
O 2
5
3 4
CH3 9
O
Figure S2. 1H NMR spectrum (500 MHz, CDCl3) of compound 3.
5
10
Figure S3. 13C NMR Spectrum (400 MHz CDCl3) of compound 3.
6
Figure S4. GC-MS spectrum of compound 3.
7
