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- 1-(2-hydroxy-4-methoxyphenyl)-5-phenyl-1,3,5-pentanetrione: Mp 187–89°C, 97% yield (ethanol): Anal. Calcd. for C18H16O5: C, 69.22; H, 5.16. Found: C, 69.18; H, 5.04; IR (paraffin oil) 1679 shoulder of broad and intense peaks from 1609–1627 cm−1; 1H NMR (CDCl3)(see ref. 7, first sentence): δ 3.90 (s, OCH3), 4.03 and 4.07 (s, -CH2-), 6.42 and 6.52 (s, vinyl), 6.58–7.15 and 7.50–8.33 (m, ArH)
- 1H-NMR were recorded on a Varian Associates EM-360L nuclear magnetic resonance spectrometer, and chemical shifts were recorded in δ ppm downfield from an internal tetramethylsilane (TMS) standard. Compd. No. (solvent) 1. (CDCl3): δ 4.45 (s, 2H, -CH2-), 6.48 (s, 1H, C3-H), and 7.36–8.70 (m, 9H, ArH). 2. (CDCl3): δ 3.93 (s, 3H, ArOCH3), 4.35 (s, 2H, -CH2-), 6.34 (s, 1H, C3-H), and 6.83–8.40 (m, 8H, ArH). 3. (CDCl3): δ 3.98 (s, 3H, ArOCH3), 4.38 (s, 2H, -CH2-), 6.40 (s, 1H, C3-H), and 7.25–8.28 (m, 8H, ArH). 4. (CDCl3/DMSO-d6): δ 4.55 (s, 2H, -CH2-), 6.55 (s, 1H, C3-H), and 7.30–8.38 (m, 8H, ArH). 5. (CDCl3) δ 4.40 (s, 2H, -CH2-), 6.48 (s, 1H, C3-H), and 7.18–8.52 (m, 8H, ArH). 6. (CDCl3/DMSO-d6): δ 4.70 (s, 2H, -CH2-), 6.68 (s, 1H, C3-H), and 7.54–8.48 (m, 7H, ArH). 7. (DMSO-d6): δ 4.93 (s, 2H, -CH2-), 6.67 (s, 1H, C3-H), and 7.67–8.76 (m, 7H, ArH). 8. (CDCl3/DMSO-d6): δ 4.45 (s, 2H, -CH2-), 6.50 (s, 1H, C3-H), and 7.20–8.85 (m, 8H, ArH). Integration for phenacyl methylene hydrogens averaged 2H, which depended upon solvent (sometimes less for DMSO-d6). See also: a. ref. 1b.
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