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16 Typical irradiation procedure: A mixture of 1,5-dihydroxynaphthalene
(16 mg; 100 μmol) and rose bengal (5 mg; 5 μmol) in 10 mL of alcohol–
H2O (9 : 1) was sonicated for 30 minutes. The clear reaction mixture was
filled into the glass reactor column (filling height: approx. 60 cm) and
was subsequently irradiated by two fluorescent tubes (OSRAM L58W/
535 T8 Tube; 2 × 60 W). A stream of air was injected continuously via a
capillary tube, which raised the solution level to approx. 1.45 m. After a
set irradiation time, the reaction mixture was collected and evaporated to
dryness. The conversion was determined by NMR analysis in acetone-d6.
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conditions were combined and 2 was isolated by column chromatography
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violet Company; RPR-200) equipped with 16 visible lamps (Philips
TL 8W/33-640; 16 × 8 W). Selected physical and spectral data for
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1
3
151–154 °C11f ). H NMR (400 MHz, acetone-d6): δ = 7.04 (d, 1H, J =
10.4 Hz, Hquin), 7.08 (d, 1H, 3J = 10.4 Hz, Hquin), 7.33 (dd, 1H, 3J = 8.4,
4J = 1.2 Hz, Harom), 7.58 (dd, 1H, 3J = 7.6, 4J = 1.2 Hz, Harom), 7.78 (dd,
1H, 3J = 8.4, 7.6 Hz, Harom), 11.92 (s, 1H, OH) ppm. 13C NMR
(100 MHz, acetone-d6): δ = 114.0, 118.1, 123.5, 130.8, 135.5, 137.6,
160.6, 183.2, 189.3 ppm. IR (KBr): ν = 3400, 3058, 1662, 1641, 1590,
1448, 1289, 1225, 1151, 1098, 1081, 863, 827, 762, 703cm−1. MS (EI,
70 eV): m/z = 174 [M+], 146, 118, 90, 63, 39. Anal. Calcd for C10H6O3:
C 68.97, H 3.47. Found: C 68.25, H 3.70.
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