Molbank 2011, M900; doi : 10.

3390/900
OPEN ACCESS

molbank
ISSN 1422-8599 www.mdpi.com/journal/molbank Short Note

(3-Oxo-1,3-dihydro-2-benzofuran-1-yl)phenylphosphinic acid
Ferenc Csende * and Andrea Porkolb Taxus Research Laboratory, Bocskai u. 22., Hajdnns H-4080, Hungary * Author to whom correspondence should be addressed; E-mail: csende@nanaskabel.hu Received: 14 June 2011/ Accepted: 18 July 2011 / Published: 25 July 2011

Abstract: A simple acid-catalyzed synthesis of (3-oxo-1,3-dihydro-2-benzofuran-1-yl)phenylphosphinic acid 3 was achieved by reaction of 2-carboxybenzaldehyde 1 and phenylphosphinic acid 2 in refluxing toluene. The structure of this new compound was confirmed by elemental analysis, IR, FAB-MS, 1H-NMR, 13C-NMR and 31P-NMR spectral data. Keywords: 2-benzofuranone; lactonization; phenylphosphinic acid

Phosphorus-containing organic compounds play an important role in biochemical pathways and processes [1,2], sometimes occur as natural products [3-5] and exhibit several pharmacological activities such as antibacterial (fosfomycin) [6], antihypertensive (fosinopril) [7], insecticidal [8], aminopeptidase inhibitor [9] and selective GABAB receptor agonist activity [10,11], amongst others. Recently, the addition reaction of phenylphosphinic acid 2 to the carbonyl group of a variety of aldehydes and ketones was investigated [12]. This reaction resulted in the corresponding hydroxyphosphinic acids. In continuation of previous works to develop new phthalide (2benzofuranone) derivatives with a number of nucleophiles [13] we also studied the reaction of 2carboxybenzaldehyde 1 [14]. The current work describes the synthesis of (3-oxo-1,3-dihydro-2benzofuran-1-yl)phenyl-phosphinic acid 3 as a new derivative of phthalides by the formation of C-P bond.

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Scheme 1. Synthesis of the title compound 3.

CO2 H CHO 1

H + HO P

PTSA, toluene, reflux, 3h -H 2 O

O O P O OH 3

Experimental In a round-bottom flask, a mixture of 2-carboxybenzaldehyde 1 (1.50 g, 0.01 mol) and phenylphosphinic acid 2 (1.42 g, 0.01 mol) in toluene (15 mL) was refluxed in the presence of a catalytic amount of p-toluenesulfonic acid (PTSA) for 3 hours. The solid that separated from the cooled mixture was collected and recrystallized from ethanol twice to give the title compound 3 as a white crystalline solid. Yield: 69%; m.p. 235-237C IR (KBr) maxcm-1: 3498 (OH), 3413, 3059, 2920 (C-H aliphatic), 1755 (C=O), 1740-1596 (br, P(O)OH), 1437 (P-Ph), 1287 (P=O), 1204, 1176, 1129, 1058, 979 (P-O), 891, 752, 715. H NMR (400 MHz, DMSO-d6) (/ppm): 6.11 (d, 1H, J = 2.4 Hz, C-H benzylic), 7.45 (m, 2H, Ar-H), 7.56-7.62 (m, 4H, Ar-H), 7.66 (t, 1H, Ar-H), 7.74-7.79 (m, 2H, Ar-H), 8.90 (s, br, 1H, P-OH). C NMR (100 MHz, DMSO-d6) : 79.9 (Ar-CH-P), 124.5 (Ar-C-CO2-), 125.7, 125.8, 129.0, 129.2, 130.3, 131.6, 132.6, 132.7, 133.3, 135.1, 145.8 (Ar-C-CH-P), 170.5 (C=O).
31 13 1

P NMR (162 MHz, 85%H3PO4): 36.77.

Elemental analysis: calculated for C14H14O4P: C, 61.32%, H, 4.04%, P, 11.30%. Found C, 61.35%, H, 4.01%, P, 11.35%. FAB-MS m/z: 275 [M+H]+ Acknowledgments Authors would like to thank Institute of Pharmaceutical Chemistry, University of Szeged, Hungary, for the spectroscopic measurements.

Molbank 2011 References and Notes 1. 2. 3. 4. 5. 6.

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9. 10.

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12. 13. 14.

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